@Douglas Alexander, best advice is to mind your numbers and don't fall in love with a particular piece of real estate.People get emotional over homes...

You can get the best of both worlds on cash flow and appreciation by doing short term rentals once you move out, or by doing a house hack, where you rent out an ADU or separated basement rental on short term rental platforms while living in the other piece of your house.

Thats the key, with out knowing all of this then its just a shot in the dark or having bits and pieces of info and trying to solve the financial freedom equation with out the full "picture."

I'm thinking about outsourcing the maintenance response piece to either Latchel or SuperTenders.

I'll let someone else chime in about the insurance piece. 

I would rather buy a solid piece of real estate and realize the rent potential in the short term future than just buy something for cash flow sakes."

It's overwhelming when you try to put all the pieces together at once in your head and then you get paralysis analysis, anxiety etc.

Someone should have just screwed up a piece of drywall and primed it white over that hole until the summer came.

You will certainly need a mason to do tuck pointing and likely capping of any remaining pieces left.  

If it was an amazing piece of property and/or if I offered seller financing with great terms and I marketed it well, it could sell in 1 - 3 months.I'm not sure if we're heading into another 2009, because that was a very extreme downturn, but over the past few years, most people I know have been offering a minimum of 40% of market value for land right, with many of them going even higher.