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Bear gives his coat to you when you finish his Biker Gear quest (which you get by chatting to him). Personally I kept the coat for myself as it is the highest cold resist item in the game that I can see, even above the expedition jacket. I was able to get Maisner high enough to get his beggar king vote despite not completing the bear coat quest.
I'm not sure about Don Kitty. I've heard there might be a hidden 'Drug Tolerance' stat that you may be able to increase by taking more drugs.
With Don Kitty you need to be 100% helth, 0% sick, poisoned, drunk. If not working try to go back tomorow.
Strategy perk teach Crazy.
When you increse your reputation with hobos, you can ask them to borow you money, but you dont have to give it back.
that's the thing. I had all my stats on 0 and my health at 100% but he still wasn't working with me. I even brought items with me to make sure everything was 100% healthy and he still wouldn't take me. That's why I'm confused asking for help. Thanks btw to you and others who posted here to help