Wow! I hope I don't have the problems like you ran into.
About the wiring for the winch. There's a conduit that the factory installed for winches......wasn't the wires run through that?
know to the Tires, I heard the same thing, but what exactly are you talking about "blowing them off all the time"?
and for the last question, are you glad you made this choice or not?

 

The winch wire about did the same thing on my dads prairie 700. That headpipe gets redhot.

 

Yes I am glad I bought this bike. I rode my Rincon Sunday and it felt like loud crap compared to the Brute V Twin. I have no winch yet it is the factory loom that melted and caught fire. I will probably get the headers coated and use a high temp loom or relocate it to the other side of the bike.