Keep saving as much as you can.

There is still money to be made in those areas.  

Get rid of debt, build a budget, and save.

So they raised money when they needed to from friends and family, referral network, etc, then got back to running deals.  

The mistake you're making in the math is on the first number. 20% chance of tripling your money. 

If the AC is not working you will need an HVAC company to come out and tell if it's fixable or needs to be replaced.To be honest, everything you are saying indicates you are going to create a money pit for yourself.

Find someplace to save a couple hundred.

I don't have the capitol right now to spend a ton of money on software.

I have no more headaches, there is an umbrella policy for the properties, and I can buy more properties with the cash flow without anymore personal money.

There are people in here who could have used a handful of that cash and turned it into a lot of money.