By day, I'm in B2B Software sales, but have always had a strong interest in the concept of financial freedom through the vehicle of real estate investing.I'm still very much learning & navigating, but am motivated to purchase my first property within the year - likely an owner-occupied FHA.

It is a hard to answer question without know more about the specifics of each deal and your personal financial situation, goals and risk tolerance. 

If only one qualifies, you'll have to convince the non-qualifier to walk away, with no financial repercussions. 

We have gone out to look at the property, reviewed the financials back to 2016 and met with the seller in person a couple different times.

Now getting a foreclosure, that WILL ruin their credit.When you make arrangements with the homeowner, they have some control over what is going on, even if they don’t have the means financially to rectify them (this is where you come in) time to find a place that is within their means, and the money to do it with!

I moved my business to Worcester a few years ago and it was the best financial decision I've ever made.

I just know if i don't start ill regret not taking a shot at my financial future.

I've dealt with distressed homeowners needing help over the years and know a lot from that angle, but I've become interested in flipping and wholesaling, it seems like something I could do well, which can  help desperate homeowners needing help + provide some financial relief also to walk away from their home and avoid foreclosure.

.- 3-4 units still puts you in the residential category- 5 or more units is commercial residential and most lenders will expect you to have experience and will generally have more restrictions on the lending process- A 10+ cap rate in the Boston area will be extremely challenging to find unless you are planning on a massive value add or redevelopment- No idea what your personal financial situation, but a 3 family in Worcester versus a 20 unit requires a very different upfront financial commitment.

My financial planning team and I focus our business on anywhere from new to seasoned real estate investors on managing their cashflows, giving them a financially organized snapshot of their assets and liabilities, and helping them allocate their funds to achieve their goals.