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.

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

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. 

@Andrew Freed is a good person to get in touch with about that as he is a MA multifamily investor who does a lot of meetups.STR is a tough way to start right now because in most markets the table stakes to be competitive are very high.

the market is tough right now, with prices high, rates high, demand high, and inventory low. 

it's tough everywhere and it's really, really difficult for a new investor to do remotely especially when they really don't plan to go in person.