Lat last year, city council added restrictions that makes it very difficult to buy a property purely as a short-term rental and they grandfathered all the current ones into place.There are a LOT of houses with guest houses / cottages / carriage houses in the back in the downtown and old colorado city area.These are what we have targeted since you seem to get more bang for your buck.

Go out to lunch, grab a drink with people who you may not usually do that with.

My whole reason for entering real estate was to go into commercial real estate, own income producing properties that kick off cash flow each month and create a lifestyle of pure abundance for my lineage.

3) What happens if one of you drinks & drives, killing someone and getting sued by the victim's family?

The $3000-6000 is purely a fee paid to the lender that you never get back.

Regardless of how remote the OP is and how hard it may be to find a Contractor, the worst thing to do is to crawl into bed with a guy with a drinking and an attitude problem.

I like the panhandle for some nostalgic reasons but if I'm looking at it from a purely investment standpoint, I would probably go somewhere that has 20% or more. 

If your goals is purely cashflow, then the appreciation shouldn't be a focus anyways.

A typical 24 year old (similar to what @Caleb Heimsoth said about going a different route) will find him/herself at a bar on the weekends, drinking and staying out late.

My little brother had several since he was about 14, first saying he was 16 and had a license to drive babe's cars, and then when he was 16 saying he was 18 to break curfew in our city, then when he was 17 to say he was 21 so he could drink and buy alcohol.