It's usually much easier to pay a small monthly fee to have a professional manage your property.

you may find it beneficial to avoid paying lender fees over and over again, on 3 properties though if you go with a lender that doesn't charge a ton of junk fees then you'd save doing it separately. 

My current rent I pay is only $500/month.

Rent would be ~1,400 to 1,800 / month which is above market rate but housing is in very high demand and price is in line with what seniors who live on their own would be willing to pay based on my conversations with local Real Estate Agents. 

AND they will pay $1000s to learn it.

What did you have in mind for expanding your portfolio?

The owner had no money from the deal to cure the lien, and because we were already passed our 1031 exchange identification deadline, we asked what the payoff was and ended up paying out of the door $112k to close this deal.

No need to pay $1500 for it.

So far we have collected about $280,000 but the borrower has been unable to pay us off.  

Quote from @Levi Perl: Hi,Curious if anyone has what to say in terms of how to calculate which one is more worth it: to cash out refi on a Long term rental now at 70% LTV, and walk away with X amount of positive cash AFTER paying all debt, (X is a positive number and significant amount for me), which will allow me to potential get another long term rental and grow portfolio faster, or wait 4 months and cash out 80% LTV, giving me DOUBLE than X.