A friend of mine ended up in a tough spot because he didn’t realize that improvements could be included in the exchange value under certain conditions.

That sounds like a tough spot to be in!

Trying to BRRR in todays market is pretty tough. 

These leads ask tough questions about the market and aren't satisfied with generic answers like "it's a good time to buy."

It is tough to find and usually takes some work, but that's the pocket of the market that makes the most sense to me. 

As a fellow Northerner, I tend to buy in the Southern half of the US for 2 reasons:1) you get much higher year-round occupancy rates in the South & it’s simply tough to earn a good ROI in the North if your place sits vacant for a big chunk of the year2) Culturally, the Southern half of the US seems to be a lot more accepting of STRs regulation-wise.

Energy workers on an irregular work schedule? 

Your new potential guests are insurance companies for homeowner displacement (flood, fire), buyers looking to move to the area but not sure where they want to be, sellers who want to sell but have nowhere to go, contract workers in the area, adjunct professors on a semester job, etc.

However, it's definitely been tough to find solid deals that cash flow well as of late, at least on the long-term side I find it to be true, and counting on potential increased demand is a tough investing strategy. 

Trusting lenders, agents, and contractors can be tough, but building a solid team and doing your due diligence will help ease that process.