I am also a licensed real estate broker with Nottingham Realty Group and I have had a lot of success helping investors (both local and out-of-state) buy investment properties, repair them, and either lease them to quality tenants (BRRRR) or sell them as a flip (BRSR).

Boston is bigger than Portland, but point to our recent success and the regulations we put in place. https://www.portlandmaine.gov/2029/Short-Term-Rental-Registration

He explains that the secret to success is far more boring than we like to admit.

Curious if anyone has had any success with this?

Not having any formal accounting or bookkeeping education and not having much success trying to learn from YouTube videos,  I decided to go with an accounting firm that does Quickbooks training. 

Hey Andrea, I haven't gotten a software application yet but what I have found to be very successfully is combining free resources.

Fear of success and all of those cliches might apply.

This area requires good tenants screening to be successful. 

See my blog on The Tenant PhaseTo be a successful landlord, and maintain that excitement that you had when you first began, before you knew the ropes, you have to have all this in place, and you MUST AT ALL TIMES STICK TO THE RULES OF YOUR CONTRACT, YOUR LEASE AGREEMENT.

I am currently using one that i found on BP and he is great but we haven't had any success.