The key factor is ensuring the property qualifies for favorable tax treatment by adhering to IRS rules regarding short-term rentals and material participation.For the 7-day rule, the IRS requires that:The average guest stay must be seven days or less for the property to qualify as a short-term rental.If the average stay is 30 days or less, you must provide substantial services similar to what hotels offer, such as daily cleaning or concierge services.Regarding material participation, to further classify the income as non-passive, you must meet one of the following criteria:You spend more than 500 hours actively managing the rental in a year.You manage the business yourself and spend at least 100 hours, with your involvement exceeding that of any other person involved in the rental.Please note there are actually 7 ways to qualify, the above two are the most common.

Multiple FTF people involved in the process, found all of them highly responsive to getting the deals closed on time. 

The reality is this is not simply a real estate investment decision it also involves personal lifestyle, life changes, and other factors. 

GET HIM INVOLVED on anything you purchase!

Knowing my end goal is to move to another state (Sperryville or Staunton, VA) and 3-4ish hours away to start a small hobby farm, does it make sense to pay off these properties rapidly in the next 5-6 years so that I have a total clean slate from a lending perspective in order to finance the land, house, and buildings, or does it not matter?

Real Estate can offset taxes if you plan your involvement correctly.

So you're the guy cleaning up the yard, trashing out the house, working the rehab or supervising the rehab, learn some of the work you could do without much time...paint, demo, basic repair, cleanup, etc.   

Purchase price: $4,000 Cash invested: $15,000 Bought land with 5 mobile homes on it cleaned it up now it's my construction yard.I would like to buy the land behind me and convert it!

The family land deal would be slightly different, but the other deals may or could possibly look something like this:We have a local workers housing crisis and many want to get involved to help.

I'd love to expand my network and connect with local investors, contractors, wholesalers, and anyone else involved in the real estate scene.