The building is 100 years old, but solid with regular maintenance and updates.

I suspect that DSCR lenders are more likely to exercise the DOS option when transferred.

They have to keep nose clean, there now in the system, tax's and all regular everything.

I'm not saying you'll be working a lot all the time, but you'll regularly have late-night questions from people checking in, for example.

By the time you add in the $120/month for their regular fee - they would make $2,640 in a year with 1 tenant placement.

I've bought a ton of homes pre-foreclosure and at auction, happy to be a resource on that stuff, plus we just launched Bid Pirate, which is the one place online for NH, where you can see all the upcoming foreclosure auctions in one spot - you can learn a lot from the regulars at the auctions........ get after it, sister!

I thought the regular "free" Stessa account was ok.

Quote from @Richa Wardhan: Regular lender financing, we have paid off 70% of our mortgage on the primary residence so we were loaned money without any issue. 

I'm considering investing in STR in Hawaii to diversify my investment portfolio (mainly for capital appreciation) as well as it being a regular vacation place for my family.

Keep in mind that tenant screening, regular property maintenance, and understanding the inspection requirements for Section 8 are crucial for success.