People in the north can get really screwed if, for example, their property is out of service during the peak summer season when they would typically earn all of their revenueA lot of Northern places are FREAKING OUT over STRs & STR regulations & they don’t seem to be very supportive of it.

It's the payback requirement on the 401k that is going to screw me up.

Sometimes you screw up and maybe work harder than you should but as long as you learn the lesson and make progress that is what is important.

I provide in "special provisions of my lease" that anything under $100 is tenant responsibility.I also clarify a list of common repair examples that I expect tenant to repair, and a list of common repairs I would rather make myself.Tenant: smoke detector batteries, filters, small plumbing leaks under sinks, clogged drain, loose handles, loose screws, pests (toilet handle is a little odd but I would likely take care of it.)Landlord: Major leaks, sewer smells, roof leaks, water heater, hvac, cracked tile, broken faucets, broken toilets."

The entire rest of the valley they are banned and my best guess is even those areas won't last long and the owners there will get screwed as they clamp down more every year.I want a ski rental badly but it's just not worth the risk to me. 

That way they can screw you on the final month's rent.  

I just simply think he never had any intention of closing the loan, and I don't need to hear "why would someone try to screw you out of 1300$ on a real estate deal".

The property is not the most “renter friendly” - it does not have A/C, has mostly carpet, has original windows (~30 years old), is in an HOA community (which can just be a pain to deal with, plus the fees), has a broken sprinkler system, the electrical wiring is all screwed up, needs an electrical panel upgrade in order to put in A/C, has a swamp cooler (aka an evaporative cooler, which is more of a pain for me than anything), and the list goes on.My major question is whether I should just give up this property with the hopes that I could find something through a 1031 exchange that maybe does have some of these things that make a property more “renter friendly” like A/C, new windows, hardwood floors, a functioning sprinkler system, etc.

Hopefully it’s their own properties’ income they’re screwing up and not unsuspecting customers’. 

You don't want to break that trust by screwing up the paperwork.