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Once a halfling attacks from behind an ally in a battle, I find it odd that the DM would allow him to hide behind the same ally again and again. If anything the shadow would give him away. The GM is the ultimate arbiter on whether a player is hidden or not.

Start as a Lizard Folk Barbarian. Make sure your dex is 14, Have a richer party member buy you medium armor. Then start taking levels of Ranger. Every morning before you finish a long rest, cast Goodberry with all your spell slots. Every morning after you finish a long rest, cast Goodberry...

The problem with dumping strength on a Heavy Armor user... Plate armor - 65 lbs Shield - 6 lbs Adventurer's kits vary but you may be lugging around 30 lbs Clothes - 3lb Healer's kit - 3lbs each extra pouch - 1 lb Every 50 coins - 1 lb Carrying capacity if you have 8 strength - 120 lb.

Are you telling me you never assassinated a monk by equipping him with Hide armor in his sleep? All you have to do is use the disarm rules in reverse.

If you start as a Sorcerer, you'll have proficiency in Constitution saving throws. Tempest Domain grants Heavy armor proficiency, so it doesn't matter when you take the first level. I would take Mountain Dwarf instead of Hill Dwarf. Starting with 16 Strength and dumping dexterity or leaving it...

Just watch out for those Raging Barbarian/Bard Wrestlers. They will laugh at your puny attempts to escape.

Remember, your blade song ends if the enemies grab you and force you to don a shield. You sure you want to dump strength?

That's pretty tough man. He's probably still playable, though. If you aren't attached to him, play him recklessly brave, and you may find yourself rolling a new character!

You could always take a level or 3 of Rogue for some extra skills, dash and hide without spending KI, and a little extra damage when using a shortsword as a monk weapon. 5 levels for the reaction to take half damage makes you reasonably tanky.

Lizard Folk monks Better Unarmed damage to start, and can choose for their unarmed attacks to be either piercing, slashing, or bludgeoning. And you can eat prisoners.

Intelligence based Warlocks would fix a few issues with power-gaming. But if you are doing house rules you can just ban the Warlock class altogether if it is a problem.

Those stats seem low, if you did point buy, that is only 19 points! (Mtn Dwarf +2 str, +2 Con is included, right?) If dual wielding, increasing your Strength is better than taking the feat. (+1 to hit and d6+1 is better than d8) If your Wisdom was at least 13 I would recommend a few levels of...

I would take Resilient Constitution at level 4 to help your party. It will push your concentration checks into auto-save territory, so you can go into melee and keep those spells running regardless of the damage you take. Bless at 2nd level for 4 party members is a serious increase to the DPR of...

Depends on your party. If you have a crossbow expert assassin with sharpshooter, his build only works with party support giving him inspiration and casting magic weapon. Unless your DM is fast and loose with the magic items.

Barbarians also don't gain the benefits of Rage while wearing heavy armor. 3 levels of Swashbuckler Rogue would give you sneak attack against an enemy you are grappling off on your own. Personally I prefer taking Bard for expertise.

With Polearm Expert it does well enough. Druids don't need to be good at melee. It's really booby prize for not giving them Shocking Grasp. Clerics are halfway decent with Shillelagh in a campaign where specific weapons are hard to find. I know in Curse of Strahd, our 22 Wisdom Life Domain...

Are you optimizing for damage or for group utility? Because the level 6 Paladin feature and the various bard features like Song of Rest, Cutting Words, Expertise will have a much bigger impact for your group than an extra 4d8 damage per short rest from dumping Warlock slots into smites...

+1 for Valor Bard. You get better slot progression, an extra skill, expertise, bonus action Inspiration and extra attack for 6 levels. Even 1 level dip gives you 4 prepared spells and ritual caster, so you'll have useful features right away.

I would ask your DM if you can drop the level of Rogue for a level of Fighter or Barbarian. Either one would give you access to extra attack after 5 levels and proficiency in Constitution saving throws. To help you maintain Hunters Mark. Fighter is the only way you are going to be decent at...

RP optimization I guess? You can be an Urban Ranger, ask your DM if you can take Cities as your Natural Explorer environment. Other than that, choose 2 different humanoid cultures as Preferred enemies, and ask your DM if you can learn both of their dialects if you choose Human twice. For...