Depending on what percentage your commercial Lender will loan you against their new appraisal, the usual 70% means that you wouldn't get all your original $85k back  at refi.

The goal would be to rent weekly roughly what the mortgage costs or more depending on what the numbers are and the market will support. 

Credit score is good.

There are some non-legal considerations as well depending on what kind of public image you want to put out.

Tired of job - want to get out eventually.I currently rent as we just moved and didn't want to buy yet.Credit score is 800+My question - what is the best way to go about financing further deals?  

@Allen Fletcher is right on in his assessment of the actual tax being dependent on past use (actually 500K tax free is the top exclusion if you're married and have lived in the property for 2 out of the last 5 years) and future strategy (depending on your path you could exempt all or part of the tax in a 1031 exchange).Your accountant paints the current picture better than anyone.

I’ve spent the last 13 years or so chasing the rabbit hole of success in the 9-5 world — successful I suppose, depending on the metrics you use to measure that sort of thing.A couple years ago, I dipped my toe back into the real estate investing world.

If your retirement utterly depends on having adequate cash flow from your properties, any downturns will cripple you.

Obviously it depends on the area and the motivation of the sellers. 

-Pet rent Depending on your building you can add income by allowing pets and charging for them.