I don’t want the property to appraise low and not have enough money to get when I cash out.

Selling it now vs renting, will give your dad more money and he won't have to worry about renters or cap gains. 

And using the hard money for the second one.

Most people don't sell an STR that is making them a ton of money so odds are it could look better, although they could be selling it for other reasons.

Our offers include clauses allowing us to do our due diligence before closing and protect Earnest Money Deposit (EMD).

Anti-money-laundering laws are largely to blame.  

I was on BP Money Episode 325:  https://www.biggerpockets.com/blog/money-325For some reason the signatures in the Forum seem to assign random podcast numbers to past guests, I’ve noticed this with other people as well.

If the deal goes south and you have next to zero money in the deal, selling a short sale or walking isn't as risky for you since you aren't losing much.

Does it make money?

You can still make good money, but it's not as much as most people think.