My main goal is it be able to retire at age 40 from my main job and work entirely on my real estate portfolio.

I've consistently written about the forces of nature and her current and future effects on the real estate market (even while often being ridiculed and politicized on this very site for it) regardless: I personally moved and invested in coastal Oregon in 2018 from Venice Beach Los Angeles partly as a result of the trajectory of climate and have assisted several clients that specifically purchased on the Oregon Coast for their own 'climate havens,' investment and future retirement homes. 

We will both keep our W2 employment for the near future just looking into getting an extra income or make our retirement easier.

@Kyle Atans  or PHX when building stopped dead cold and they deported half the construction workers who happened to be 80% of the tenant base.. same with central CA building stopped  no deportation though :)I just bought in Vegas for semi retirement and tax purposes I kind of like were it sits now.. but no question your timing of that market was impeccable.. !!! 

Additionally, since my parents are nearing the retirement age, I'd like to prioritize low-debt, high-cashflow deals.

So if you had 20 of them, you're talking about a huge retirement kicker that you can build.If you're up there higher in age (i.e. 40's or 50's), then the long play doesn't make as much sense. 

So, I'm interested in the Kissimmee Florida area for a potential retirement home.

I have a good FT job in education administration, but I want to retire asap, focusing on RE (so, not really retiring, but you get the idea).

Right now, I'm drowning in much better opportunities and by the time I wrap those up, I'll be retiring on some riverfront property that I like. 

Im down to 6 loans right now and scaling back going to retire soon .