Because obviously if the price drops, then the seller loses out and buyer favored.

This change alone stands to gain me ~$150k+ in equity due to the increase in NOI.My concern is that firing this PM may prove complicated due to his status as a tenant.

Problem statement:My question is What is the BEST method to cash out equity, as one home has 300-400k sitting available before we get to the 80% LTV.

You can either use your profit to buy a property free and clear or use your profit as your equity requirement if you're obtaining a new loan on the acquisition.

Now I have the confidence I've been waiting for, I'm not making any money from this I did it as a favor but things I learned are worth more than money.

We are reasonably handy people if a house needs repairs we are willing to take on a task and put in sweat equity.

However, it appears as though you have more than $100k in equity...just waiting to be used. 

Obviously he has some equity/value, depends on what price he’s willing to sell for. 

It's better to get one with equity in it.

But that's the only way to grow. putting yourself outside of your comfort zone is the only way that eventually this stuffed becomes your comfort zone.Keep your long-term goals and the big picture in mind - you are not only living for free you are also building Equity every single month.