I've had good success flipping 2-3 properties a year to supplement my income.

I am currently an L1 certified ASE master technician and originally was looking to supplement my income but the more I learn the more I see that working on cars will be merely a hobby in the near future!!!

Or, if you love the business, maybe become a realtor/flipper/wholesaler/etc. to supplement the rental income.

BTW don't see any active SFH in Allston at all with the only recent sold near your criteria was $410K.The multi might be a better way to go to get a little more house and get some supplemental income.

My short and long term goal is to progressively reduce the time I spend at work and supplement my income from investments.

You guys sure do get insanely cold out there for long periods of time, so be careful on the assumption there unless you can lock in a thermostat setting and tell them to use space heaters to supplement ($$$ to run, but its electrical so not your deal).The nice thing with multifam is kinda what you alluded to.

The word is that the tenants understand the pickle you are in as a landlord and may supplement the payment to keep you happy as you could always take a non-Sec 8 tenant for more rent.

I can create a passive income stream or flip some houses to supplement my income.

I am still interested in implementing this now that Section 8 and other programs like HUD-VASH housing supplements for Veterans are more common and a decent source of steady income if you find the right properties.

I became interested in real estate recently due to pay issues in my job, and a strong desire to supplement my income.