And it's a rather low bar to get over for anyone wanting to continue to wholesale. 

Down payments on DSCR purchases can be as low as 15% right now, and as you noted, they don’t impact your DTI.

I haven't filed a claim all these years but insurance is for the what-if and to be used for the high-ticker items, but chances of damages exceeding the 5% is low.  

So assuming your son has low debt, then he should be able to qualify for a house in the low $300K range. 

Hopefully that slide stops due to seasonality in spring, but if we are in another year of stagnation prices may plummet.

I don't know your specific market all that well but have you done some analysis on your ADR during the high season X your high season occupancy rate and determined whether taking lower priced slow season bookings vs letting your property stay vacant during the winter averages out in your favor?

A $60K down payment will get you a $300K property (assuming your income is high enough and debt low enough to qualify for a $240K mortgage).

The risk for investors became low enough for them to be really interested in the project.

In my state i have no such requirement on security deposits but i question the feasibility of doing this as well as how will anyone know as long as you have the means to pay the tenant their deposit when they move out. most banks charge for low balance accounts.  

I made a low offer and it was accepted.