So here is the situation... I DM a game for about 7 people in 5e after running a really long 4e game. The game is episodic where people can come and go as they like so we can play every weekend. My group consist of a lot of players that like building optimized characters and a few that prefer the RP portion. At this point the party is mostly level 5 with 2 level 6 characters. When starting, we all rolled stats where the party got pretty lucky.
One of my players is running a half orc barbarian/monk multiclass (he is homebrewing the monk archetype he's running as well) and came to me the other day with a concern I'm not sure how to address.
He missed about about a month of play and ended up falling pretty behind when it comes to equipment. All of the DMs Guild adventures I've found seem to be magic item loot heavy and he's worried that his character just can't keep up with the party. Normally, I would just fix it with some gear tailored to his character but I'm running into a few mental hurdles.
He purposely built a non optimized character to fit his concept. This is great but we all built our characters together and has played with us for 4+ years now. The rest of the party is incredibly optimized with what they rolled.
Keeping with his character, he's deciding to run his character in a way that prevents him from really using his multiclassing. He won't use Ki when raging and wont frequently rage.
Using the DMs Guild adventures I'm seeing how powerful magic items really are in 5e and I really don't want a players feeling behind to "catch up" by needing magical items. That will break the balance of my game and lead to a slippery slope of magic item creep.
At level 5 I think he is just at a bad level with his multiclassing. Missing out an an ASI (Barb 3, Monk 2), feat, and first "keystone" ability is going to set you behind no matter what. Especially when picking 2 classes without a good sense of synergy.
So, I'm torn on what to do. Do I make sure something like Ogre Gauntlets or Bracers of Protection are in the next loot drop or do I see if we can work through this level and see if we get better. Or, do I tell him to bring up his B-Team character (advantages of running a mercenary group) until his primary character is at a level to feel equal?
If the player is set on keeping this character then by all means let him. I have a player who went Monk/Warlock and feels like her character isn't working out very well, so I've got some idea of what you're trying to do here.
Solution 1: Talk with your player and find ways that the two classes could synergize. Monk/Barb are two classes that can really work well together if used properly, maybe they just need a new set of eyes to help work out the kinks. As you have mentioned Rage and Ki are not being utilized to their fullest, help them see the benefits of using them more often and how they can tie into his story.
Solution 2: Use an NPC "mentor/tutor" to show them how the combination might work. Using a "master thief" to teach a rogue how to rogue is trope, but it helps the player learn to use their abilities in different ways than they'd been doing up until then.
Solution 3: Doing a side quest where the player has to prove his worth and in return they'll be rewarded with some trinket that gives them a +1 to a lower stat. Use this in tandem with solution 2 and you end up giving the player an item that they may want and you can teach them more about the character's abilities.
As always, just spitballing ideas here, maybe they'll give you some sort of inspiration.
If the player is set on keeping this character then by all means let him. I have a player who went Monk/Warlock and feels like her character isn't working out very well, so I've got some idea of what you're trying to do here.
Solution 1: Talk with your player and find ways that the two classes could synergize. Monk/Barb are two classes that can really work well together if used properly, maybe they just need a new set of eyes to help work out the kinks. As you have mentioned Rage and Ki are not being utilized to their fullest, help them see the benefits of using them more often and how they can tie into his story.
Solution 2: Use an NPC "mentor/tutor" to show them how the combination might work. Using a "master thief" to teach a rogue how to rogue is trope, but it helps the player learn to use their abilities in different ways than they'd been doing up until then.
Solution 3: Doing a side quest where the player has to prove his worth and in return they'll be rewarded with some trinket that gives them a +1 to a lower stat. Use this in tandem with solution 2 and you end up giving the player an item that they may want and you can teach them more about the character's abilities.
As always, just spitballing ideas here, maybe they'll give you some sort of inspiration.