Good luck with your decision!  

Don't let tax implications drive investment decisions.

Having family with trades is a huge benefit, even if they don't do the work, utilize them as a resource. 1.

What decision is your significant other leaning towards, what stress is in your relationships?

Just say no.I would almost never do this trade unless all my downside, including potential unknowns, were completely compensated for. 

But I don’t want to trade my time managing a business for a relatively small net income.The mistake many people make is comparing a real estate investment returns with a real estate business returns.  

If there is a repair needed I can either do it(some may not be as handy) or I can call a skilled trade guy.

Eventually, properties with ADU's will begin to trade and those sales will set the comps. 

Southbridge and Webster are cheaper as well.There will be obvious trade-offs in terms of location / amenities and price but i have seen good traction in all of the aforementioned locations.I'm looking for househacks for clients around central Mass and while they're not impossible to find by any means units in Worcester are typically trading at $225-250.

Have recently started a renovation company with a friend, both of us successful business owners and talented in the trades.