I would ask for the last few years of the Tax Return Schedule E for this property to see what their total expenses and net profit was.

Quote from @Derrick E.: My free advice, don’t pay for some real estate investing course.

Quote from @Scott E.: Great post Jake.

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.