I am trying to figure out whether to use a tax software like Turbotax or go with a tax accountant to do tax filling this year.

For one applicant, when I looked up his court history, I saw that he once initiated a negligence lawsuit against a pizza place because he slipped on their floor. 

(Opposed you the short term vacation rental which limits to 90 days, for non owner occupied properties) DCRA hasn’t begun issuing licenses yet - they have a RFP solicitation out, or maybe it just closed, for someone to build a software application to issue and manage the STR licenses.

Learning to self manager my first rental property... which software would you recommend?

Yes those you could bend rules based on the tenants, kind of.I said kind of because I know some landlords encourage their tenants (and applicants and others) to talk to each other. 

Here's the applicable law, taken straight from Maine Legislature, Maine Revised Laws, Title 32, Chapter 114: §13003.

I don't know the Brazilian market, but I could see this model potentially being applicable in Mexico, Ecuador, Peru, or Kenya, which I do know.

Has anyone been in this particular situation with this software?

I was just about to do one myself when they stopped taking applications due to the Coronavirus but this is temporary. 

@Loren Jacobs Thank you for the response, the JV concept seems the most applicable aside from me just saving the down pmt on my own.