There is a massive opportunity cost when you do the work yourself as oppose to contracting.

I was forced to use the same questions and phrasing that you guys came up with, as opposed to my own.  

I was able to walk the exterior (vinyl siding) will need to be repaired/replaced soon.

The exterior of the cinder block was then covered with brick or rock in your case. 

Upcoming capital expenses include paint exterior, hvac getting old, and no way to know how long the drains will last.

Plus we decide case by case what we feel like doing.What we do ourselves (in general) - We paint both interior and exterior, hang and tape drywall (but on the last big drywall job we hired a couple of guys to hang the ceiling pieces), we fabricate and install trim, hang interior doors, install some flooring.

I also think you could consider staying with the original exterior color, and perhaps painting the existing shutters, and adding shutters to the other windows where there is room (there are some good primers that will stick to the shutters).Likewise, can you keep the original entrance awning (perhaps raise it a few inches it looks really low in the photo?)

IE  NY NJ and other common wealth statesas opposed to states like GA and MS and TX were your in and out of foreclosures in 6 months or less.And for those reasons in my HML days I would never ever consider lending in those type of states.. you basically cannot have enough equity to cover your short position if the buyer defaults.. those invested with POL are finding this out.

Is there anything specific I should be aware of as far as the way lenders look at refinancing a property with a note carried by the owner as opposed to it being from another conventional lender?

I am paying a little more because all my loans are commercial loans as opposed to personal residential loans.