Anyway, my autism is unstoppable!
[EDIT] Fuck i missed one lmao. I ain't gonna fucking redo it though, screw it.
As an experiment i decided to try it with pure sleep, but it didn't work that well, the reason being he wakes too easily. On some enemies, once the sleep effect starts, you can just hit them over and over and they don't wake up. This allows you to basically chain one sleep after the other. Now with the bear it's not so much that you can't chain sleep on them in itself, but that if you wake them up you have to restart the sleep build up, and if you accidentally hit them again one too many times, you have to do it again, so you have to hit him very carefully to make sure once you see the sleep effect you stop right away, which is not exaclty easy on this spazzy bastard. So not to make the fight last until eternity i decided to cut down his health with rot and bleed first:
As you can see, i can easily put him to sleep at least three times before his resistance gets high enough to run into the problem i just pointed out, that of risking to reset the sleep build up by hitting him one too many times, but i think three sleeps is enough to just kill him with rot. Just rot him (and you can use rotten breath if you catch them asleep, their wake up animation is long enough to allow you to get a full charge), put him to sleep, go ride around picking up daisies, rot him again, put him to sleep, and after that you should have at least one or two most easily attainable sleep effects to just kill him with little risk.
Keep in mind as SL1 with a +4 St. Trina Sword i'm not doing as much damage as i could so maybe if you do it with full upgrate and capped stats you could just chain sleep him as long as you don't accidentally reset the build up. From gives you so many hints to use sleep on those guys that they probably designed them to just be bypassed like that, put them to sleep than just move on, you don't even have to bother trying to kill them. Pretty sure that's supposed to be the intended way to deal with them.