@John Brown Running a short-term rental (STR) on a subleased property, often called rental arbitrage, is feasible but requires careful planning.

. - cash flow is difficult now with long term rentals even if you pick markets that have lower purchase prices than Boston.

Does anyone have any experience with furnished mid term rentals?

Short term rentals are legal when the host is living in the same apartment as the guests and there are no more than 2 guests staying with the host."

I think I'm in a pretty unique situation and am trying to figure out the right hoops to jump through to move forward.Long story short, I'm trying to tap into the equity of the rental property passed down from my grandparents that is held in an S-corp which is co-owned by myself, my siblings, our cousins, and an idiot uncle.

Are you wanting to grow a portfolio of rentals without coming out of pocket to acquire each?

I'm not very intimate with the markets to the north and south, but I would start looking at price to rent ratios and decide what type of rental type and terms you want to invest in.

We are now doing short term rentals but we're thinking about changing to a small wedding venue. 

Quote from @Devin Peterson: Quote from @Kieran Dowling: Hello,My parents helped me by my first rental property .

Make sure pool is listed on your insurance policy.