Make sure to sign an affidavit that you're selling a qualified primary residence when selling, otherwise the title company will report it to the IRS and may trigger an unnecessary inquiry.

It's expensive to implement this strategy and, in my opinion, unnecessary for beginners.  

Any suggestions on how to prevent this in the future?

His timeline doesn't make sense to me, so you might get lucky and find a 25 year old power of attorney that may or may not be enforceable in your situation, but you also might find one that is much more recent and put in place to prevent the transaction you are trying to engage in.

Does this include some preventative measure to avoid those late-night maintenance requests?

I feel like I could have done better in the due diligence stage, so what have you done to prevent these types of situations?

My concern with the more expensive property is that it would eat up most of my savings, preventing me from purchasing another property unless I find an alternative financing source.

So for these size homes, the rental payment would be right on board with the regular payment standard plus guaranteed however, I feel after reading your post that considering the offers for under qualified individuals puts myself and family at unnecessary risk.

It's not preventing me from buying, but I have adjusted the way I deal with tenants. 

It may not be a foolproof answer, but it will show that steps and measures were taken to prevent such calamities before they occurred.