Once you get into the details you'll find more than one thing that is not ideal or doesn't work as you had hoped.

My goal is to analyze/find a deal between now and June, purchase in June, rehab and hope to have it on the market end of 2022, early 2023 (I've also heard this isn't a ideal time of year?)

Ideally I would love to get into the world of multi-family rentals with rehab potential- who doesn't love a good rehab project?! 

It is not the norm for a buyer to run into an agent or broker who the wisdom, expertise and the 'want' to be a good match for a buyer.I deal with agents and brokers every day and when speaking with them I know for a fact that even brokers who made several hundred thousands dollars from my purchases still send me crap properties for sale, every day, and these brokers know for a fact the properties are crap before they send them to me.My shrink always told me that I am an idealist, buy we don't live in an ideal world.

You’ll want to work with a broker who has an idea of historical and current deals, but most importantly and I deal of what’s upcoming that may have room for you.

If you can get a 4 unit and a basement, that would be ideal and create major cash flow and equity creation, plus you can not worry about a property manager and boost your yield and avoid rent stabilization laws. 

Ideally, my first deal won't require a huge cash outlay because I want to leverage primary residence lending options.

@Bruce Woodruff I understand completely that this state is not ideal for landlords, but this will be my only investment property because I essentially want to live there.

I'm looking to purchase my first VRBO property and ideally looking in the Siesta Key Beach area in Florida. 

If I'm correct, what's your ideal price range and area?