I've always been intrigued with learning about real estate & making it a part of my retirement.

Determine a goal you’d like to work toward financially, is it “financial freedom” (whatever that means to you), buying a business, becoming self employed, becoming a full time real estate investor, having enough cash for your kids college education, having enough to retire, becoming a centi millionaire, etc.3.

This will give you a clear picture of any liens or claims that could affect your plan.Consider Subject-To Financing: This gives you more control over the property, simplifies resale (especially if an FHA buyer is involved), and eliminates risks associated with the seller retaining legal title.Weigh the Risks of a Land Contract: If you’re looking to avoid closing costs, a land contract could work, but ensure that the seller is financially stable and cooperative.

On the beach side there has been recent development with a Jimmy Buffet retirement community and the Hard Rock soon to open.

They all use variable debt because (theoretically) it is a lower rate than fixed and it gives them 3-7 years to "stabilize" the property, "value add" by renovating and jacking up rents, and then selling the asset at a huge profit to either another REIT who thinks they can do even better or (less commonly) to a Blackstone or similar, someone who might theoretically hold it for 10 or 20 years as a stable, income producing asset. 

My father is 68 and looking to retire from managing and owning a 54 unit rental business in our town. 

Plus, if you're interested in stable, long-term tenants, many investors in these areas, including myself, have had success with Section 8 rentals.

could do really great charitable things with that kind of money) and more than likely even if retired at a young age, I plan to continue investing and scaling. 

I'm looking for somewhere that at the very least, would make a great winter home when I retire in fifteen to twenty years....  

Nobody expects their retirement account to cash flow while they are working.