Quote from @Scott E.: If I read your post correctly, you are currently running your guest house as a STR, but you do not currently have proper insurance in place.

Also looking for R E Agent / Investors form out of state to give me some insite of your market. 

I entered the market after a successful e-comm business sell out with $80k.

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.

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.

Juul, an e-cigarette company, was initially founded with the mission to help cigarette smokers break their addiction.

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.