I stand to collect a significant windfall in early 2019, and I am contemplating how best to put the money to work.

Just think about it - before Charles Schwab, you would call your financial advisor/broker and pay $200 to sell/buy a stock.

As @Aaron Klatt mentioned above post, the caveat is that you are financially responsible :)

With all things financial, it's about making an informed personal choice.

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.