If you hire a Property Manager they can sometimes help arrange lawn and snow removal service.  

The cash flow is a bit sub par on this one and I anticipate some larger expenditures coming my way in a year or two so I'm contemplating this as an option.

For your next step, you might want to look into seller carry arrangements and joint ventures.

I have the credit, experience and the knowledge on how to underwrite the deal to show their ROI in this arrangement vs a traditional sale. 

I know the hotter markets are in Sylva and surrounding area.Been contemplating how Franklin would do in STR myself.

A more realistic expectation is 24 hours which will ensure we can arrange any repairs or corrections with a team, handle it in person, etc. be curious how this plays out as I worked for local developer for a while and developed several properties in Alexandria (Specifically old town) and while the city is challenging like any city - they were mostly realistic.

I think this arrangement can suit both parties, he wasnt going to be able to keep the house but can still live there for super cheap.

People interested in this type arrangement probably don’t have access to $150,0003.

Most lenders will vary how aggressive they will get based on the experience of the operator (you), but I don't know any that will lender to someone who's never done a spec build like you're contemplating.

Most agency loans will expressly forbid such an arrangement, so if they found out, the odds of having the loan called would be very high.