Now purchasing a home with cash is always good b/c obviously cash is king but also I think the part you might've missed is that, the money your utilizing on these home's won't actually be yours, but the banks or whatever institution you used to fix the home or make its value worth more.

You've only owned it six months, so you probably haven't dealt with vacancies, maintenance, or capex, but you should be setting money aside for those things.Your partnership agreement (if you have one) should address exit options.

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

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

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.  

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.

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.