I'm also concerned about the real estate market as a whole.

Even that manager needs to be really hard worker and skilled in so many different areas...sales, marketing management, hiring, firing, reservations, computer skills, and more.   

Depending on the seller, you may sweeten the deal, by letting them know that they don't immediately need to cash out, or can partly cash out.

From both a real estate and STR perspective, the key to success will be choosing the right market first.

If the latter, how does that look on a day to day in terms of operating, marketing, and the ownership structure?

If you do not qualify, you would then look into if you would qualify with renting your departing residence. 75% of the lease will be used to offset that departing residence mortgage. as you mentioned the timing of renting the place can absolutely be tricky so you would hope you do not have to do this.Finally, and I guess would be sorta of a trick, but we do bridge loans on occasion in this case IF you can qualify once you get the property rented at market value even if debt to income ratio is too high before it is rented.

We are a massive appreciation market. 

Are you looking into certain investment strategies to begin or certain markets? 

Found it through a broker on the market.

Guest breaking down their markets and strategies gave me a lot of insight.