Quote from @Angel Dejesus: https://www.mass.gov/how-to/reactivate-or-reinstate-a-real-e...Call their phone number and ask.

If any portion of the building or structure is occupied by the taxpayer, the gross rental income from the property must includes the fair rental value of the unit occupied by the taxpayer.IRC 168(e) defines a dwelling unit as “a house or apartment used to provide living accommodations.

I actually wanted to own 5000 of them.. and probably could have gotten there but holy cow Juice no way worth the squeeze.

For myself, I own an e-commerce business so I am self-employed.

You do not need a negative cash flow deal to show a loss on your Schedule E.

So to me Pinot land can only go so far.So wine tasting in the WV gets a little tiresome when every winery basically only has pinot and maybe one white. and or they buy their grapes from E Washington to make different varietals.

I e filed claims with both VRBO and AirBNB and had no issues having them paid.

It's pretty much a war zone there and I've had to communicate mostly by e-mail and text as cell service is about non-existent, and all the roads are closed so there's no driving over there and no gas even if you did get there. 

I operate in the E coast of central Florida and we have a significant dip in Sept into Thanksgiving, and then stay full for the duration of the year.  

Which ever home you choose as the main home it will be a tax deduction so it should work out in the long run.Another thing to consider is having two primary homes does not offer a great Schedule E option where you can have the bigger tax shelter.