5e combat system too simple / boring?

My experience I have yet to see a 5e combat run meaningfully faster than 4e would. Out of a 3-4 hour session, we still spend 1-2 hours in combat. If we only get a single combat in a session, it might drop down to half an hour, but certainly no less than that.
So putting these three points of data together, am I correct in deducing that a typical 4E combat for you runs half an hour? If so, I think your 4E experience is faster than most people's. (Which wouldn't surprise me; you of all people probably know how to keep 4E combat humming along, since you both love the system and have played a lot of it.)

We use a grid (via Roll20, so all the math stuff, distances, and grid positions are handled for us), but AFAICT no variant rules.
I play 5E over Roll20 with a grid as well, and we use the variant flanking rule (my players are coming from 3.5 and they really missed flanking, so we decided to add it back in). Most of our big boss fights last an hour or so, with non-boss fights being shorter. This is slowed down both by our tendency to joke around and by the fact that I'm not really proficient with Roll20. Fights go a bit faster when we can get together face to face and actually play at a table.

Just a bit of anecdotal evidence, for what it's worth.

I'm afraid I'm not quite clever/funny enough to come up with real zingers for vicious mockery every turn.
The bard is annoying the hell out of me too. I don't have any idea what round after round of vicious mockery would look like in an adventure. Every bard is a quick-witted comedian?
When it comes to the Bard, if you choose to play every Bard as a comedian, that is a choice. I am playing my Bard as slightly more serious (though I cannot fully resist the lure of insiuating their lineage contains hamster dna or that a certain smell lingers on their parent's breath).
I'm playing my bard as a foul-mouthed little halfling whose insults just happen to resonate with the primal words of creation. I got a Shakespearean insult generator book for Christmas last year, and every time I do VM, I pick one of those to hurl at the enemy. There are free generators online too, for anyone else who wants to try this technique: Here's a Shakespeare one ("Thou viperous motley-minded horse-drench!"), and here's a more piratical make-your-own version that you could print out and keep with your character sheet ("Ahoy, you pig-faced, jelly-boned freebooter!").
 
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When coming up with pithy lines for vicious mockery is a challenge, I just switch to descriptive roleplaying and say, for example, "I unleash a string of jibes so insulting that they can affect the mind of the recipient."
 

I'm playing my bard as a foul-mouthed little halfling whose insults just happen to resonate with the primal words of creation. I got a Shakespearean insult generator book for Christmas last year, and every time I do VM, I pick one of those to hurl at the enemy. There are free generators online too, for anyone else who wants to try this technique: Here's a Shakespeare one ("Thou viperous motley-minded horse-drench!"), and here's a more piratical make-your-own version that you could print out and keep with your character sheet ("Ahoy, you pig-faced, jelly-boned freebooter!").

That's the problem. Vicious mockery fits that type of character. I'm playing a bard that is a dancer and a singer. She doesn't jest at all and wasn't raised to jest. She is a very proper lady. I've decided her particular use of vicious mockery is harsh song notes. Her Cutting Words is more of a song of defense. Her inspiration is uplifting music that resonates within the mind until the inspired uses it. It's a change of flavor that accomplishes the same thing. That's what I encourage to bards that don't feel like using the flavor text of the abilities exactly as written.
 

The PCs got slaughtered, basically. They failed to get to him in two minutes. Viktor, Selene, and Vlad took down Lora and Winston pretty quickly and they rose as vampire spawn. This overwhelmed Bulette who went down soon after. Lady Wilhelmina resigned herself to her fate to be by Vampenstein's side for an eternity of undeath and we rolled credits. Fun ending.

That's good to hear. I'll post my creature after I use it and let people know how it went. My players may come to this forum. I don't want them to know anything about the creature until I use it.
 

The DMG lists a few options:

Roll Initiative Each Round (w/Speed Factor): Adds randomness and uncertainty to combat, and demands greater choices of action (since high-weapon damage and higher-level spells now trade of effect for speed).

.

The other way instead of having to bore yourself with Dice roles and always having Dex builds with the advantage is use what some people call the popcorn method where the players decide who goes first and then that player picks who goes next and so on (or sometimes I pick who starts and then they go off that so it is changed up). Nothing gets more boring then rolling the dice for initiative every round when the rogue over there has a +4 to dex and you the wizard has a +1 gee yea great . I found the popcorn method kept players better engaged; players where able to use some strategy and hey they get to make the choice not me or some random dice role. Just my two cents

(I never understood why initiative did not go off the classes main stat)
 

My experience of 5e, such as it is, has not illustrated that the combat system is particularly interesting, and can in fact get quite boring. People frequently tout the speed of combats, but I have yet to see a 5e combat run meaningfully faster
Speed is what saves it from being as boring as you might expect just from looking at the relative lack of options. And, you really should be seeing that difference, because it's prettymuch hardwired in. Attacks hit more often, saves fail more often, damage is higher, spells more powerful, and hps, at low level, anyway, are a lot lower. A turn may or may not go faster depending on who's taking it with what character under what circumstances, but there should simply be fewer rounds in most combats.

And, despite having taken community advice on the kind of character to play as a 4e-fan+5e-skeptic trying to give 5e a chance, I still feel like I have far too few choices.
Obviously, you should be playing a full caster. How short of choices can you feel with a character who chooses mod+3 dailies to 'know' vs at most 2 or 3 and casts 2 or 3 three of them vs 1, while still getting multiple at-wills? You still get to choose a Background, too. And, though you don't get a feat at 1st level, you aren't paying any 'feat taxes,' either. It seems like, as long as you want to play the right concept, you have a lot of choice relative to 4e. Nothing like 3.5, but that's not where you're coming from.

We've only gotten up to level 3, but combats are still mostly meat-grinder-y, leaving me terrified for my character's survival--a non-ideal situation when I'd specifically made the character for being decent-to-good at melee
By 3rd that should really be tapering off noticeably. Give it to 5th, if you don't see a complete turn-around by then, something's wrong.

But you do bring up one way that 5e combats can drag on a bit - and it's familiar to the point of nostalgic to those of us who played AD&D. 1st level characters are so fragile, and the new backgrounds/traits so encourage players to invest in their characters, that just letting them die like flies doesn't sit well with every DM. You can't just dial down encounters to the point their 'safe,' that'd not just be comical, it'd give far too little experience. What 5e does leave wide-open is 'ruling' in favor of the PCs' survival ('fudging') and that can make a combat that should have ended swiftly in a TPK drag on quite a bit.

I habitually describe my character's actions, so there's no improvement to be gained there, though I'm afraid I'm not quite clever/funny enough to come up with real zingers for vicious mockery every turn. Which, incidentally, vicious mockery the vast majority of what I do, because I have so few spells to work with, I feel compelled to hoard them until they're truly needed--mostly cure wounds, or the occasional faerie fire.
My players had a lot of fun with vicious mockery - it probably accounted for most of the mechanically-inspired fun they had, at 1st level, now that I think of it. But, yeah, focusing on the responsibility of the band-aid role will not provide you with a lot of fun. Cast spells like you would dailies in 4e if you had that many of them: whenever they'd be particularly helpful. Use Cure Wounds only if getting someone back up is critically important at that moment. Not only will it leave you more actions to have fun with, it'll run the party out of hps faster, so they'll rest sooner, and you'll re-charge your dailies.

The most frustrating thing is that I feel like I am supposed to have a substantial toolbox and lots of bells and whistles, but I'm either too terrified to use them, or can't justify the expenditure on so few threats (or so small a threat). For example, I'm playing a Dragonborn, but I have yet to use my dragon breath--because the only fight I've been in where it would've been worth using, I was bleeding on the floor by the end of the first round and never got the chance. I have allegedly powerful utility spells like sleep, but they succeed so rarely or so minimally, I can't justify spending the slot when it could instead be used to keep one of my allies from getting pasted.
You're definitely not managing your slots optimally. Healing is best used to bring an ally up from zero, when their next potential action after you revive them will be vital to the party's success. Anything less than that, and you can probably find a better use for the slot.

I don't dare get in melee range most of the time, because almost every time I have, I've been brutally punished for it
That's fine, casters are supposed to be melee-shy.

Yeah, I can definitely agree with that. It's one of D&D's numerous "chicken-and-egg" problems, and also one of its "all solutions MUST be extreme"* problems, unfortunately. (Really, it's "all solutions in the past have been extreme, so an edition which mainly prioritizes dressing up traditional mores must follow suit." But that's not as pithy.)
Not sure I follow the parenthetical, there...

I...find the second option you suggest hard to comprehend. What does the events during other peoples' turns matter, for my enjoyment of what I'm doing? Whether or not the things they do are interesting/dangerous/boring is...entirely orthogonal to whether I am turned off by the combat
Staying engaged includes staying interested in the whole battle, including what everyone else is doing. Though some groups can handle just playing on their turns, that's usually what gives a player a sense of combat being 'slow' or 'boring' (that and having to wait longer for their turn because everyone is having an individually-interesting turn). If you can enjoy the whole game, not just your 1/4th or 6th slice of it, it's less boring. In 5e, party composition matters. If you're all playing complex 'interesting' casters there'll be more time between your turns, if you've got some quick-turn classes in there, you get a larger share of play time in proportion to them.

It has been difficult for me. The CRs aren't much help. Some high CR creatures are pushovers, some lower CR creatures very tough. Encounter guidelines in the DMG aren't very helpful.
Coming from 3.5, you should be accustomed to compensating for comparatively rough CR guidelines. The key is not to trust them, and to go ahead and adjust on the fly, since no amount of pre-planning is going to be perfect. 5e frees you to do that, since it seems to have effectively undercut the Cult of RAW that gripped the 3e-era community.

Getting the right level of challenge has been difficult in this edition since monsters seem to fall into the too weak to too deadly category that doesn't seem to have a great deal to do with CR.
It is, indeed, like the olden days. More a matter of feel than numbers.

It's a failure for anyone that wants to model a grittier wound system. That's why it's always required optional rules to incorporate those concepts. I don't think hit points model 'plot armor.'
Then they've always been a failure, for you, of course.

I'd love to see those numbers, but I imagine no way to get them other than memory.
iserith is very much a storyteller, I doubt he has any entirely-un-planned deaths in his campaigns, and don't doubt that the body count is little-impacted by edition. 5e certainly gives a DM more lattitude to play in that style than 3.5 did, or rather, community attitude now vs then, thus.

In 1E and 2E getting snuffed was one missed saving throw away.

In 5E past the low levels, say 1-4 or 5, death is rather rare so far.
Of course, in 1e, saves got genuinely easier as you leveled up.

Unfortunately, our DM is big on playing RAW and without any frilly/extra rules, in part because he's somewhat new to 5e. That's the main reason why we started at level 1, for example. (Some of our players being new to TTRPGs in general also factored into that choice.)
Ooch. Not a great choice. Level 1 is really, strangely, not for beginners - it's where the game is tough/gritty/deadly/frustrating or however you want to couch it. Level 3 is a better place to start all around. A little overwhelming to jump into a full caster at 3rd, maybe, but there are a few simpler (sub-)class choices.

And playing RAW 5e is almost a contradiction in terms. The RAW tells the DM to ditch the RAW and make rulings, instead.

Also, part of the reason for our combats being so meat-grinder-y is that his other 5e group regularly punches well above its weight, while ours struggles to punch at weight. Game's currently on hiatus for the holidays, but he has repeatedly expressed his dismay at our group being unexpectedly easy to overwhelm. Thus far, his efforts to adjust have not quite felt effective, but it might be a problem of perspective for me.
5e really did 'Empower' the DM, but that does mean that the success/failure/excitement of the play experience is more on his shoulders than the system's. FWIW.
 

Speaking of Bardic Insults, I insulted an Ogre in our last session with the words "You dumb, me laugh at you ha ha ha." because sometimes you have to tailor the insult to the target, and to an Ogre that seems to mock them more than referring to them as a "tempestuous canker blossom on the bowels of humanity." Sadly, however, he rolled an 18 for his save and decided to walk away from the fighter with a pike, and over to me where I proceeded to get smacked down to 1 hit point...

Using Roll20, our combats don't take too long because most of us have macros set up to help with things - my cutting words macro, for instance, is a one-click action that takes a couple of seconds while I'm adding insult to (avoid) injury. Having fewer dice to roll definitely speeds up combat, and in the case of 5e it's done a decent job of eliminating how many dice you need to roll all the time (the one exception being 5e loves D4s too much)
 

That's the problem. Vicious mockery fits that type of character. I'm playing a bard that is a dancer and a singer. She doesn't jest at all and wasn't raised to jest. She is a very proper lady. I've decided her particular use of vicious mockery is harsh song notes. Her Cutting Words is more of a song of defense. Her inspiration is uplifting music that resonates within the mind until the inspired uses it. It's a change of flavor that accomplishes the same thing. That's what I encourage to bards that don't feel like using the flavor text of the abilities exactly as written.
I think that's an awesome solution. (BTW, my halfling bard also happens to sing beautifully--he's a former choirboy--but he has the urchin background, which is where he picked up his more colorful phrases.)

Someone should make a Jane Austen Insult Generator for the more prim-and-proper types who might want to use the cantrip!
 

iserith is very much a storyteller, I doubt he has any entirely-un-planned deaths in his campaigns, and don't doubt that the body count is little-impacted by edition. 5e certainly gives a DM more lattitude to play in that style than 3.5 did, or rather, community attitude now vs then, thus.

Unplanned deaths are definitely a thing in my games, to the extent that I don't give a single flumph if a character dies. I just try to plan ahead for what comes next, generally in the form of having backup characters ready to go so the player's participation doesn't take a hit. I care about the players in this regard, not the characters.

The way I generally design things is to make fighting your way through a challenge "hard mode." If you take the time to engage in exploration and social interaction, you can find ways or things to reduce the difficulty. Or there will typically be alternate goals to achieve victory. I pull no punches otherwise and never fudge. When I decide that rules and dice are in coming into play, I abide by their results. (Otherwise I wouldn't have rolled in the first place.)

I have had it where players want to kill off a character because that's what would make for the best story, however. And this may be more what you were referring to. This doesn't happen too often though.
 

I have had it where players want to kill off a character because that's what would make for the best story, however. And this may be more what you were referring to. This doesn't happen too often though.
That's the sort of thing I was expecting, given what I recall hearing from you over time, yes. I'm a little surprised at the pull-no-punches/never-fudge stuff, but I'll take your word for it.
 

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