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For the first issue: Simplifying yours commands will help, but I think you are fine. Rather than commanding them to use their "optimal" attack, simply commanding them to "attack/kill this Hobgoblin" should cause them to attack it with the simplest means. If one is next to it and has a sword, he...

If you require a reason to identify the value of foreign or high value objects, the PHB lists several ways to help. Related tools such as Jeweller's, Glass-Blowing, or other related tools would allow you to add you proficiency bonus to the check. Buying a magnifying glass specifically aids in...

It would be more about the players and how they acted rather than the characters that would make me walk. There are lots of different ways, and everyone likes different stuff. But it's a lot easier dealing with a well-meaning player with a low moral character than a hostile player with a Lawful...

If you want to try a half-measure before adjusting class features, what is the player's background? I think it was Charlatan that gave proficiency in forgery or disguise kit and the feature is to have a False Identity. Or you could make a custom background to fit the flavour he is going for...

Maybe next time they clear a dungeon and find a treasure hoard, all those coins are sure locked up in a fancy looking chest. Plus, there are those local rumours of a petrified mimic in the closed down museum on the edge of town...

1) If it is with 2 PCs I let them decide. Between others, I either use higher Initiative mod. or just call it depending on the situation. 2) A creature can split their attacks among any targets on it's turn. So if it can use three attacks, and the first attack kills a PC, it still has two...

For the goliath, are you looking for something that will encourage him to cast more magic, or to suit his current play style? Perhaps a bearskin coat that gives him resistance to cold and bonus to intimidate/survival could be a good idea, especially if he hears about a rogue Polar Bear that is...

I think one or two lines in the statblock would be more than enough to show how to play certain monsters. Traits give a good idea how to play and show the strengths of many monsters: Orcs are Aggressive, Hobgoblins are Martial (Disciplined), Goblins have Nimble Escape (Cowardly), Gnolls attack...

So an interesting situation came up in my game last night. We have a Fighter with his darling Halberd and my own Paladin with his recently acquired Whip from a now-smited (smote? def not smitten) fiend. This was our first combat where we were able to maneuver a bit, and we use the DMG Flanking...

You can just treat them as any other group of intelligent, sentient creatures. Using the stat block of a Giant Bat (or even larger birds) could be a good start, and then add in a trait or ability that fits within your lore/how their society is. Bats might be able to strike in complete darkness...

I like the idea of adding some complexity to differentiate weapon choices, but having to cross-check each attack in each encounter with a magnifying glass over two printouts is a bit much. I suggest focusing on either Armour types or Weapons and adding effects to change them. Something to make...

HP isn't just about how many hits something can take. A storm giant could take way more physical punishment then even the best of non-magical human warriors, and it's ridiculous to think otherwise. But a CR 12 Warrior Antagonist? He has inner reserves of resolve that focus his mind. He has...

Abilities like Pounce often allow the creature to make a bonus attack on a hit as well

Beholders are powerful and intelligent creatures and can be seen as individuals or NPCs depending on the campaign. You could have the Beholder have a certain theme depending on his profession, location, or how he acts. One Beholder who has gone mad (well, madder than usual) could have Tasha's...

You could use them similar to Eberron's dragonmarks. When a PC finds a rune/shout, they absorb that power and are able to use it. Depending on the spell or what level they are you can upgrade the power in strength (ex. use as higher level "slot", the damage cantrips receive at each new tier) or...

A big part of the Barbarian's damage comes from Rage and their Reckless attacks. Rage scales with level, and adding in the fact that at later levels Barbs can increase their Strength past the normal cap of 20, giving them better damage, attack bonus, etc. Add in the fact that Barbs can take a...

Why would dangerous, magic-wielding creatures with access to all manner of spells, still produce a great number of humanoids that rely on swords and other melee weapons?

First thoughts: ​Overview Saving throws: Should have one of common Dex, Wis, or Con, and one of uncommon Int, Str, or Cha. You have Dex and Wis, both common saves. Weapons: You start with a rapier or shortswords, but aren't proficient in them until level 3. You should start with prof in them...

I think Weathercock brings up an easy way of doing it. Look at the weapons your setting has and think of how they are used, and why melee combat isn't preferred. Modern firearms are great at wounding and injuring people. But maybe a plasma rifle kills infantry instantly, or melts through vehicle...

It's part of the cost IMO. If you take a specific skill eg. Animal Handling, and the campaign expects a lot of riding/beasts/creative uses, then it is a viable option that benefits a character with Wisdom over Strength. Some situations (pulling an animal away) may allow the use for either skill...