My reno strategy was literally I can get this at lowes and have a handyman do this and handyman do that I can paint this and I can paint that.... 2 months later at 2 interest payments later and a fat bill from my not-so handy handyman...

Unfortunately due to state law I can not offer you compensation for the referral but I would love to take you out to eat some time to show my gratitude!

The repair costs can eat you alive out of state.  

Orion is right on, its great to have the motivation and some cash to do something, but one bad investment will eat that right up. seems like you are in the time in your life when the gambles can be made and live minimally. do it now, take the risks now, but make sure they are calculated. 

A manager for a 35 lot park will eat into your income.

The high taxes on both are eating up your cash flow and the HOA on the condo is killer.

.******* I am not a doctor or lawyer or advising anyone to go start eating popcorn ceilings or huffing asbestos******

If it don't eat the hay, buy it.

Basement waterproofing on the entire foundation outside will eat into my potential profit three fold. 

Those items eat up Benjamins fast.A 1950s electrical system could be a 60 amp, fuse box, two-wire setup - completely inadequate for today's needs.