And if it were set up where everything went through a title company so the buyer pays the title company, they manage the buyer's loan (from me), and the title company ensures my mortgage is paid without my direct involvement... what parts of the transaction would feel risky or not worth the headache to you? 

The more mature platforms that are designed for landlords/property managers include Rentec Direct, Buildium, Appfolio, and Rent Manager.

Quote from @Jonathan Greene: Quote from @Jamie Parker: Quote from @Jonathan Greene: Those are video game calculations.

Should I find a few buyers before I go out trying to find sellers, or should I start with sellers, then look for sellers directly or bring it to other wholesalers?

You can acquire that debt across the direct property and / or the DST/TIC.  

People looking to book may see that it is a brand account and look up the brand, then book direct.

But as of the last 6 or so months I seem to be losing direction.

Quote from @Alexandra Helms: @Dziko ThundeHere is a video published by a local agent (though I believe he actually moved out of the area) a couple of years ago that you might find helpful - "https://youtu.be/LPNIl_vLkWc?

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I found this property through my network of local real estate professionals and direct outreach.