Should you decide to do this full time and do more than 1 flip at a time, private lending and fix&flip loans will be the way to go.

I have reached out and spoken with the HOA management property manager myself, and just keep getting BS excuses and no sense of urgency on this matter. 

Pensacola is a great market for investing and the number of properties available right now is up so there are actually some on market properties with potential. 

When I worked with a property management company, we had someone buy a unit (single family) that had a STR and marketed it as a STR.

You are losing money on both properties. 

Driving by a property today to see if makes sense to walk.

I've personally done just about every rehab scenario, properties I've lived in, properties bought as investments and even properties bought at auction.You've gotten good advice from folks on this list.

First, all properties that appreciate the appreciation is based on the property value, not the equity. 

I would look at the DSCR loan as the first option.By the way, I suspect you are going to be disappointed by any refi appraisals   ADUs typically appraise poorly   JADUs can lower the property value Vs having the space as part of the primary unit.  

Good morning @Joshua MartinGreat thing about a VA mortgage is you can do an IRRRL even after you have moved out of the property!