The goal was always to retire early (which may still entail “working” but just not having the requirement to).

How does one go about researching what this entails?

@Lindsey Clark, as noted all three options entail the same plan.  

This could entail sending notices to yourself for a meeting that only you will attend and only you will be voting at... 

I am aware of the 1 year primary residence contingency that the FHA loan entails but is it true that you have to have 25% of the equity to have tenants in a duplex as well.

What exactly does that entail - is that 'money' just available funds for another property? 

Much prefer the the word help and the energy it entails.

Place a call to a few other property management companies in Houston and ask them what their listing service entails and what they charge. 

Instead of asking if you should get it, you should research what being a real estate agent entails and if it will benefit you.if you have another job, you will likely be doing the real estate license part-time.There are two main reasons that people get the real estate license1) To make money via commissions2) to have access to the MLS and view properties(I don't think this is a good reason as you can view sites like zillow/trulia/redfin)Real Estate investing is hard in itself, no need to spend the many hours taking classes/exams to complicate the investing portion of real estate.

I have a decent amount saved up and will definitely have enough reserves in case anything come up.I am leaning towards starting in Florida since they have friendlier laws for landlords but need to do more reading into what that entails and if its worth sacrificing my ability to visit the property whenever I want.What areas in Florida and NY do you think I should focus my research in?