@Roger MatthewsHomestead laws and the Homestead exemption for property taxes have nothing to do with each other. 

There a ton of pitfalls that can just crush you. from bad tenants from hell to city regulations that are impossible to figure out to taxes to bad rehab jobs etc.

Trying to see if I should pay more lawyers fee to get the money judgement. 

On the other hand, a SFH is generally farther from the water (I'm trying to stay within golf cart distance to the beach), has less amenities than a condo, and higher property taxes, but seems like it would offer more appreciation than a condo.

Good choice :)Being able to start a journey of deferring that tax will compound for you as long as you keep the new properties or do a 1031 whenever you sell one. 

What I mean by this is considering how much your down payment returns to your net worth (appreciation, loan paydown, tax benefits, AND rent avoidance).

If you combine them then the courts (and tax courts) deem it a loan and cause a foreclosure action and you to be taxed differently than if it was a lease property. 

I am looking for a lawyer to know more about the redemption rights of the property.

If your already in a high tax bracket, then the commission will be taxed at that rate which may be more than the capital gains.

I am doing my own taxes for the first time in years with Turbo Tax program for 2022.