High w2 salaries, $100k cash, experienced DIY'er, advice needed

[Ryan Detzel]

Our story.

We're high salaried employees. We have excellent credit. We have zero debt except mortgages. We currently own two homes with mortgages ~$700k that we don't want to part with. We have $100k we're willing to start investing with, ideally we only use half of that on a cheaper place but we're in the Boston area so it might not be easy. We might expand our search out to western Ma or even NH for cheaper places. I've rehabbed three of my own homes and two others so I'm very comfortable doing most renovations myself. I would like to start building some passive income so I've been looking at multi-families but I'm not opposed to a single family or even a flip if the numbers work. 

Given this information, what kind of advice can you give me on where to focus/start? I really want to buy multi-familes as I feel the rental income will give me the best opportunity to continually loan and buy and grow. My ideal situation would be to buy a two family that needs work, do it myself (3-4 months) and then have a cash flow place.