The plan is to aggressively pay down the LOC with the cash flow (or refinance with enough appreciation).

That will give you a great foundation, and by then you'll know what direction you'd like to pursue in your self-education.Once you know a bit, start going to local RE meetups or REIA meetings to improve your knowledge with face-to-face interactions with people doing work in the industry.Everywhere around Boston is expensive, if you're still going to work in Boston and want to live within short commuting range, you'll have to do some aggressive hunting to find the right deal. 

They'll have a ton of housing supply it seems. 

There is an endless supply of books, pod casts, guru info training classes etc. 

What's appropriate for an aggressive investor will look horrible to a conservative one (and vice versa).I'll give you my perspective as a conservative investor.

To me, 8% is too high and could mean you're too aggressive on your rent hikes. 

Smart investors whove been there and done that, are always saying “look at the supply and demand.”

The lack of supply in the 3 to 4 unit properties can be overcome by the massive SFH that can be converted to 3 or 4 unit apartment buildings.

The rehabber can get a home depot line of credit (or similar) if they don't have funds to buy the initial supplies. 

This gives you an idea of the supply of houses in the area and a starting point at how long it will take to sell.