I am also considering a live-in flip on a large single-family home, and possibly renting out some rooms during the renovation if I can find friends or tenants willing to put up with the renovation (I don't like the uncertainty of the cash flow in that scenario if I can't find tenants).

You can either keep the extra cash flow piled away for any future expenses or prepay the loan so you jump ahead in your amortization schedule.Hope that helps and good luck growing your portfolio!

Key considerations include:Zoning and Permits: Check with local and county zoning offices to ensure that your lot allows for manufactured or modular homes.

I can definitely tell you there's still a lot of positive cash flowing and 1% rule deals and you get amazing appreciation.

Real estate can also provide the additional benefit of cash flow.

Agreed with the others - looking at MA there aren't any special tax considerations that I would worry about having someone local, you could work with someone just about anywhere remotely. 

We are going to convert our current primary into a rental, and it will likely cash-flow well enough (including capex, maintenance, vacancy etc.) to also cover the loan repayment on a $60K home equity loan amortized over 25 years.  

If you have an 800 FICO, low leverage, and high cash flow, the rate should be a little lower.

I’m looking for something relatively turnkey that can cash flow strong.

Well, it’s the key consideration for sure, but simultaneously, you need to factor in operation overheads before sitting back and enjoying the passive income.Handling tenants, arranging repairs, maintaining properties, and making statutory payments for taxes and inspections are some of the costs you may not consider when dealing with rental properties.