My advice is to look for and explore markets with great macroeconomics - just like here in Columbus.

The owners may agree to carry part of the financing, but you won't need them to stick around to transition operations.After acquiring the properties and assets you wish, you would either run your own business, or part-out and resell some of the assets.From your post, it does not sound like parting out the properties is a viable path and where you admit to having no experience with vacation rentals or the resort business, you might want to explore purchasing the business with the current owners hanging around for a bit to help you get your feet wet.Regardless of approach, it needs to have legs to be worth pursuing.

We live in the panhandle (PCB, FL) but are interested in exploring the greater Tampa/Sarasota market!

We are sandwiched between well known hot spots and its an ideal location for someone who wants to explore the beach life or any of the down-town areas nearby (Los Angeles, Long Beach, Redondo, Manhattan, Southbay Etc), new build with modern amenities, washer/dryer in unit, full sized fridge, dishwasher, professional range cooktop, queen bedroom, full standing shower, large kitchen, full sized couch in the living room, private front patio. 

@Nicolette YorkRecommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

Group insurance: Look for insurers offering discounts for insuring multiple rental properties or join a local landlord association to explore group insurance options.The key is to strike a balance between cost savings and maintaining adequate coverage to protect your quadplex investment.

I’m currently reading Brandon’s book on creative financing and am interested in exploring the possibility of obtaining a home equity loan.

Research emerging neighborhoods, find properties using MLS, Zillow, and Redfin, explore financing options, form partnerships, analyze deals using BRRRR calculators, and manage the rehab process.

You might also want to explore other options like Real Estate Investment Trusts (REITs) for more flexibility or even direct ownership of smaller properties if you want a bit more control.

I would explore there.