Here is what I think needs to happen: 1) Obtain HOA approval and amend by-laws to gain official ownership.

Also, the quality of the property will directly affect the amount of rent you can obtain. 

Is that something most firms even entertain?

Years ago when my wife was getting her education she was presented with a choice to further her education and obtain her doctorate or settle for a masters .She knew it would mean many more years of school (12 years altogether) and well over 100,000$ more in student debt on top of what was already owed .

With regards to non-performing institutional notes, I get asked weekly by various folks to provide them with my sellers and avenues for obtaining tapes.

You mentioned Josh and Brandon so you've probably already found the BP podcast but if not, it's both entertaining and informative!

Again, there is no problem there either since presumably you have obtained a power of attorney from the seller at closing which entitles you to sign any insurance proceeds checks.

Just another entertainment idea - I signed up for Spotify's family plan and gave each property it's own email address so I could enable multiple user devices under one master account. 

His realtor mentioned this cheap 5 acre property that he needed to sell for a woman who obtained it when her brother passed away.

If you are able to acquire the lien for 10% of the amount due, you might obtain a potentially advantageous equity position on the property.