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It's interesting, on the one hand I feel like I crave more flexibility, customization and more decision points. At the same time, I very much do not want a Skyrim-style system where everyone just starts as pretty much identical blank slates and develops their character entirely in response to...

What is it about being low level that makes that particularly true, do you think? As opposed to saying that the first few sessions define the dynamic, independent of starting level?

I find levels 1 and 2 sort of pointless for veteran players, particularly for a group that has a session zero or can otherwise communicate about their character concepts before starting. There's little mechanical variety at those levels so the game aspects of the game tend to be pretty samey...

I mean at that point why not just tweak warlock and make everyone play one?

I tend to preplan my "build", but rarely stick to exactly what I plan. I like getting to make decisions about my characters' mechanical development at more than one or two points, and wish 5e had more granularity in this respect (e.g., break up feats into smaller features and pick them more often).

I think it might be helpful to work backwards... Let C(n,m) be your expected number of hits with n attacks to come if you have m images remaining. Then (assuming for simplicity that we pre-cast MI) we are interested in C(n,3) as compared to C(n,0). Let T(m) be the chance that an image is...

I would lean toward option 3 since it's easier to multiply abilities than divide them, but cap SR resources to their current number of uses within a given encounter.

Keep in mind also that heightened spell doesn't do much good vs enemies with legendary resistance, which any boss type will have at this level.

Hexblade 1 / Divine Soul sorcerer might be worth consideration also. "Favored by the Gods" fits with your backstory, and then you can cherry pick your spells between the cleric and sorcerer lists to fit your theme. You can still get spirit guardians, but it doesn't have to be your automatic...

Death Cleric is probably better than Grave if you want to focus on necro damage.

Gloomstalker and Assassin pair really well together: the extra initiative boost helps you get that first round advantage, and then you also get an extra attack during that round when you have it. Plus, being invisible in darkness vs creatures who rely on darkvision means I'd pick up your ASI at...

I agree. They're spending their concentration and an invocation to give themselves advantage; seems fair.

I mean, there's lots of complexity in real combat that isn't addressed in the rules, right? This is one of those cases.

Well, not quite. Everyone else in the area makes attacks against everyone else as normal (because they are both unseen and can't see), but are at disadvantage attacking the warlock; whereas the warlock is at advantage attacking them. But other party members might still be annoyed at not being...

Ah, yeah I guess so. I've always thought about magical darkness as blocking light ("non-magical light can't illuminate it" after all), but I have seen DMs treat it the other way. I've always interpreted the rules to say that you only have to guess at the location of a creature if they are...

Also, I don't know how the OP's DM runs it, but by RAW, if both attacker and defender are blinded, there is both advantage and disadvantage, which cancel out (and also cancel any other source of advantage or disadvantage). So your allies are only hampered by your darkness if they would have had...

I certainly agree that the rules don't allow for doing this outside your turn, but is there any rules reason why you couldn't place a bowl over your necklace at the end of your turn, perhaps as an object interaction, and then remove the bowl at the start of your next turn (I would think that...

Yeah, I think it's particularly not much of an ask when you are picking a race/class combination that means you are not benefiting from half of your racial features. You could get the same stats as a wood elf, plus get 5' extra movement, darkvision, charm resistance, and some extra weapon...

If you are committed to Lizardfolk, you might consider asking your DM whether they'd be ok with you moving one of the +2 from CON into DEX. I would think most reasonable DMs would allow you to do that when you're taking a race for flavor reasons (and clearly not picking it to powergame). Other...

Another observation: it seems to me that you are gaining almost nothing mechanically by going lizard folk here, and you are sacrificing DEX by not being able to start with +3. The lizard folk benefits are very redundant with monk features: unarmored AC boost (does nothing if you have WIS of 16...