And with the example you used of being able to save 100k per year, do you really think that there’s gonna be that much stress relief from a paid off mortgage when you’re making kind of money?

The main property will be my primary residence.My biggest question is, what kind of foundation would you use, (that is to code and will pass inspection/permits in Charlottesville) that is either relatively easy DIY or cheap to outsource.

But I kind of did what you describe..

What kind of deal would you "typically" be able to find.

Hey @Mike Pepperday, AirBNB and VRBO are your best bet to see what kind of demand there is for STRs in general.

I have researched the different kinds of loans for this but I would love to speak with any lenders or other investors in this area.

Thank you kindly. 

Make sure you already have an exterminator to call though.Also, our lease states that tenant only has 30 days from MoveIn to report pests of any kind.

This includes converting it to a rental property or refinancing into a different kind of loan. 

To piggyback on Jay's point, generally speaking I think the kind of personalities that are really good at real estate are the opposite of the kind of personalities that are really good at self promotion and presenting.