Families don't want to move during the school year and snow is an issue.  

2) Given my age (47), goals (cash-flow for retirement; longer-term wealth), and the fact that financing would have to be non-traditional (while I have access to a bit of cash, we are entrepreneurs whose tax returns do not look good in the most recent few years), is considering multi-family my best option? 

The issue i'm running into is that many mortgage companies will not finance condo purchases, even with a sizable down payment.Does anyone have experience in non-conforming lending that would allow me to put 20-30% down on a condo with a traditional 30 year mortgage?  

Strangely enough this one was not an ancient home either (built in the late 70s) and is worth pretty good money (150's now, was 200's at one time).

I assume you are thinking you can borrow the down payment and couple that with a more traditional/conventional type loan? 

Be ready to have a plan laid out in timeline (usually two years before traditional financing and you're saving up funds to make larger down payment during this time or pay cash to sellers directly), who will cover repairs, taxes etc. and it can be great for them to know that you would be taking care of the property as your own now (level of care) because you truly want to buy it at the end terms and exercise the right to purchase. 

I think you may have to get aggressive and find off market properties using estate attorneys, probate attorneys and other non-traditional sources for properties that aren't on the MLS. 

Insurance: $1200/YearUpkeep:$1000/YearSnow Removal/Garbage/Misc: $1000/YearMortgage Expense: 30 year @3.75% ~$1800/monthTotal Income: $48,000Total Expense: $10,200 (Property Tax, Insurance, Snow Removal Etc) + $21,600 (Mortgage)Net Income: $16,200This is my first property that I am seriously looking at.

I do like how explicit their forms are, but I can probably delete a quarter of it as not applicable.By the time we have the lease, the non-standard addendum (so they shovel snow and mow the lawn), the rules and regulations, and the lead paint disclosure, that's too many pages!

Next one is in March (hopefully less snow then) and it would be great to see you there.