Years ago I bought houses for $25k in my market.

Tremont is an excellent area with really high market rents and super high demand.  5000+ sq ft. is huge too, congratulations!

I avoid the multi-family market here, so unfortunately, I will not be a good go-to here, but I am confident you will find quality resources and help here on BP.  

Goal would be to acquire 20 rentals by the age of retirement, with some already starting to be paid off.I am in the same boat as you, and I focus on safe appreciation all day (small cash flow for safety and then focused on markets on that appreciate). 

For me it’s building connections with buyers in a new market. 

After living through the GFC and the shrinking market for local banks, they saw an opening in the market for what they call "consultative banking" like they had years before and decided to start a bank.

Access to Cash Value: A properly structured permanent life insurance policy (like an IUL or whole life) can build cash value that you can borrow against for property acquisitions, renovations, or even as a safety net during market downturns. 2.

You can achieve or even exceed your current cash flow in markets that are more landlord-friendly than Boston.

Help, I have a friend who wants to play the stock market and I don't know how to talk him out of it!

If looking to change the market value of property, well there you go.