I’m a longtime investor and Realtor from the DC metro area as well-  BP is a terrific resource to help you grow both your investment portfolio and better support your investor clients!

Is there any supporting documentation that I could have the current renters fill out prior to purchasing the property?

This is a common question among real estate owners.Let's dive in:The reality is that wealthy families often pass on real estate assets from generation to generation.For example, if one generation has an RE entrepreneur who amasses $50 million worth of real estate, that portfolio can generate enough cash flow to support multiple future generations comfortably when passed on.So, what happens if that initial investor built their empire by rapidly depreciating assets and using 1031 exchanges to lower the basis and defer taxes along the way?

I know Kilington and Stowe are strong but I thought being a little closer to major metros might help and the info I'm finding seems to support.

You might find it is overall better to do a MTR if the area can support it.Being on VRBO is a must if you keep it a STR.

As for audits, the IRS may scrutinize high-income taxpayers claiming REPS, so detailed time logs and supporting documentation for material participation are crucial.

Yes if you mean support yourself after you finish your regular job effectively using rent as a pension. 

Negative cashflow is never a good idea (even if you can support it).

When someone presents to "tap" Private-$ we want to do as little thinking as humanly possible, that's to say the burden is on you the proposed borrower to present a complete, detailed "pitch" outlining the allocation of every cent, contingencies, time-lines, data supporting each action item.

A link to FilePlace is at the bottom of every page, so it is easy to find.If you have technical issues, send an email to support@biggerpockets.com and someone will help you.