I have seen on this website answers both ways regarding this (the site administrator saying leave it in Sch A, and his colleague (also a enrolled agent) advising that it can be written off in Sch E, but that there are certain restrictions mainly -- you must have passive activity gains where the deductions are covered (no passive activity loss carry over allowed.

Are you investing mainly for cash flow, appreciation, or long term equity build?

Main issue: if you add an ADU the property becomes a 2 unit bldg., which means it’s under rent control for both units.

I stayed here by choice, precisely because of the opportunity I saw in this market compared to CA.

The main aspects of real estate that I am interested in would be owning rentals, and working as a RE agent. 

Is MA an unwise choice? 

There are people who misused their IRAs and lost money are a result of making poor investment choices or violating the rules and getting their IRAs disqualified, therefore losing money to taxes and penalties.

However, I am trying to figure out what I can do now to start the process, and how I can achieve my goals within a reasonable time frame.Like you said, would it be the best choice just to lower the payments on my current home so that renting it out would be more lucrative?

My main goal now is to put together a team for when I really get started investing.

The main skill is: finding "deals".