I am able to work as a travel doc, and she works remotely in tech, and we plan to use our combined incomes to put towards REI, as well as keeping our cost of living reasonable!

My wife and both make a high income for our area and I feel we could save about $100K per year to keep buying. 

We’ve worked diligently with our carrier partners to keep rates stable for many years.

That is why I consistently point it out.If everyone keeps calling it a loophole over and over, some eager beaver down at the IRS might decide to take a look at the law and recommend changes and do away with this.

Keep an eye on what is for sale in your market, what is selling, and for how much.

It works well if the goal is to minimize closing costs and keep these properties in the long hall. 

If you stay put for a long time, buying makes far more sense because you are eroding the purchase price with inflation, while rent will (theoretically) keep up with inflation.

Given my current situation, what are some important factors I should keep in mind?

Yes, in Florida, I would get one, it's worth it to keep you safe.

I would like to keep my current house as a rental property, but don't have the funds to pay off this one and buy a new one.