My insurance agent says I've reached the 5 property max to receive better pricing through their go-to carrier, Vermont Mutual, and will now have to bind with a more expense Massachusetts state-sponsored program.

By the way, I sent Tim & Kirk from Phoenix your way on your Lease Option program.

Also, utilize the MassSave program for any quick renovation upgrades (0% interest for 7 year loan on energy efficient household items).

FHA is a fantastic program and helps a lot of investors get their start.

Such a program does not provide you with access to the funds in any way personally or through your business. 

Most states have some kind of program like that. 

Wondering what I should do/ what I should instruct my tenant to do.

What website/program do you recommend for this?  

@Mary AnnI have seen programs before for commercial/mixed-use properties that are no income (no doc) loans but they require 30%-35% in equity/down payment and the rate is normally 4% higher than a traditional 30 year residential loan.

Duplexes do not have that self-sufficiency test.There is a program called Home Possible, which has income limits set at 80% of area median income as of July 2019.