I feel like either Bacon would drive him insane due to his hyperactive personality. Or Leonard would just be used to Bacon’s antics by this point and be unfazed. Bacon would also be very concerned over his wellbeing.
KitKat and him would probably get along a bit better. In step 2 she was pretty angsty but by step 3, she’s actually rather pleasant to be around, you still don’t want to get on her bad side though. She would totally be keeping Leonard in check though. KitKat knows what it’s like to be tired and he wouldn’t get to use it as an excuse with her. :)
Also, in case you didn’t see it, (which is reasonable because it got buried very quickly) I decided to torture myself again by drawing everyone’s MCs. So if that interests you, the post is a bit further down.