That might be the biggest hurdle - but otherwise, I'd check out "DSCR Loans" which are the perfect option for people like you looking to buy rental properties w/o W2 or DTIWe don't own any other properties other than the investment property we just purchased.

Even when sourcing a Section 8 tenant through a company like yours, what are the biggest challenges for investors in this space?

You make revenue here and there but the goal is to generate enough in the winter to sustain all the expenses for the entire year. 

It is a very well established market with solid, steady revenue, and it is beautiful to visit.

Your other levers are revenue (which as you mentioned is capped) and expenses (which congrats to you are low).

One of the biggest challenges is keeping the bathroom as carefree as possible.

I recall reading in Forbes that major foundation fixes can add surprising value, becuase it addresses the single biggest fear buyers have.. a shaky structure.From my three decades in fix-and-flips, Ive noticed how important it is to have a team you trust.. from attorneys who know probate deals to realtors willing to drive for dollars with you, scouting hidden gems.

Here is  the biggest question - I expect withholding  $1.00 of the security deposit is going to cause friction.

Two of the biggest players in this space just folded.

Once you know what specifically is stopping you, you can address it directly—whether that means learning more, asking specific questions, or just taking a smaller step forward.Sometimes the biggest hurdle is just narrowing down that fear and facing it head-on.