@Liliana Bennett most HOA boards are composed of the actual homeowners.Just like there are many DIY owners here on BP, trying to pinch every penny, there are HOA Boards trying to do the same.Guessing your HOA Board members have specifically taken many possible tasks away from the PMC in an effort to save money.

Out of money and options, he licks his wounds and lets it go for back taxes. 

I'd say the Bigger Pockets forums are one of the best places to explore how to put your money to work in RE. 

In the old days this was known as “flash money”.  

You will only have one opportunity to get money out of an approved tenant.

If you are uncomfortable investing your own cash, how will you convince others to invest their money?

I’ve got a distressed and on-market house that was recently completely renovated until the couple ran out of money (all of the heavy lifting has been done, just a few things left), and it is listed well below market price compared to surrounding comps I could find.

There was limited money left for making improvements. 

What I'm hung up on is how to make a deal work so that it produces a satisfactory rate of return for the money partner.

If your potential numbers already look good, you most certainly won't regret the money spent on a designer!