To note: 1.

A family member is also a real estate agent and would provide me with the 3% commission on the purchase of the new properties, minimizing cash outflow on the new properties.So my high-level thoughts are, I could downsize and buy two properties, which would reduce my monthly living expense by 1) a smaller primary note and 2) income from the MF offsetting a portion of the primary note, and at the same time I would be able to pull the equity I have built up in my current home, plus my current cash on hand, to further invest after the dust settles.

Do note, however, that Pennsylvania does have a law that restricts who can engage in property management activities for another person.

Not a DIY project but another option is just 1 investor that provides you a note secured by a mortgage.  

Would you guys prefer putting your money in an index fund or mid risk (9-10% return) performing notes?

If your note came due after 2007, you were in trouble unless you had a low LTV and strong pre-existing banking relationships.

The list I came up with is : Insurance, Title, Signed note and Mortgage.Are there any other documents crucial to save besides the origination documents which the MLO would have to save up to 3 years I believe.

These are also challenging areas from a crime perspective.There are 66 in Middlesex County, many are in Lowell, again, might be challenging.BTW - a note about Middlesex and Worcester counties. 

Cliff notes, after back and forth and me sending him pictures he started saying he was having a hard time with stuff and life and on and on.

His note to me last week:Thanks for the listing and the comps, but I do not see the opportunity.