I have an arrangement with my friend where I stay with him one or two nights a week for cash, and his air went out.

State and federal laws have been created just for this......sometimes referred to as rent skimming.....getting someone to QCD their house over to you with No intention of paying their mtg payments......stay far away from this. 

Remember that markets can stay irrational for a very very long time.

I saw a listing for a 2 bed/2 bath room in a ski lodge that we have stayed at before. 

Also, definitely stay away from websites zillow and Icomps for comps- those sites can be up to 70% off on their numbers.Now I don't know the specifics of your deal like beds/baths, lot size, etc, but looking at comps within a .1 of the area, I would guess you'd be in the upper 300k range.

But, we do not plan on staying in our current house forever so that doesn't seem like too much weight should be put into that.

And I definitely want to stay on budget. 

They stay in it a year while fixing it up, etc and then use the rental income to qualify for the next home with at least 5% down.

Those are people who plan to stay and make your house their home. 

Stay in school, and get a finance degree with a focus on real estate, or go to trade school and become an electrician/plumber/HVAC.Can you be successful without it?