We're loving this new chapter of our lives!

Also, if eventually you get into that house hack, and elect to self managing a duplex, triplex or 4-plex that you own/live in, you will by default learn about property management skills and no license is required to manage the property you own.To answer your specific question, yes - you can become an employee of a property management company to learn about property management and I highly recommend it!

In my mind though, since I live in NY, own the property in NY, doesn't it fall under NY laws anyway?

Almost every year it seems that there's a new bill up for vote putting various restrictions on STRs, the current one being that it's illegal to rent out your home if you live there less than 120 days per year. 

Quote from @Jordan Ornelas: My name is Jordan and I live in Lynn Haven, FL (Panama City).

I have around 70k to get started with and a government pension to live off. 

Are you planning on renting out all four units or living in one?  

My wife's grandfather owned many buildings in NJ and I have seen that 2 generations have lived off of what he did in one way or another. 

It means you buy a place with more than one unit, live in one, and rent out the rest.

If one bids on the house, lives there couple months and ends up being married and living elsewhere - this was not a violation of the HUD rules back in 2004!