Getting right to the purpose of my post, with all the relevant context: I’m 52 and living near Seattle.

We are currently living just south of Boston and are looking to purchase a 2-4 unit property in which we would live in one of the units.

However, I live close-by (30 minute drive), recently retired from my day-job, and if the loan is not too large, I might be willing to do a deal just to learn a bit more about another side of RE.  

I sometimes wonder if people just feel lazy dumping their money into an index fund in the stock market and actually using all that free time to go out and live life.

You all must agree to the same thing or else you will just end up fighting about what to do.Since your mom doesn't have it in a living trust, I suggest you do that right away.

Off street parking is typically more important for high end/expensive rentals.

 (3 convention units +  3 ADUs) * 3 lots = 18 unitsIn general adding one ADU is not a good investment because there is no more expensive residential development than a single, small unit.  

Private money may be cheaper, but may be more expensive if they are doing something that most hard money lenders wont do. 

Housing is one of those things that people like to scream about, but the reality is that there are more than enough places for everyone to live.

Just google the following: - special assessment - zombie condos - Florida condos (look for recent news)Since you are not living near the properties anyways, why not look in a landlord friendly state where the purchase prices are lower?