First steps into this resort buying mess
Alright, so picture this. I’m scrolling through stuff online one night, half-asleep, and I see this listing pop up: HHI Beach and Tennis Resort for Sale. Sounded fancy. My first thought? “How hard could buying a resort actually be?” Spoiler: Real hard. Way harder than buying that rusty lawnmower off Craig that one time. This ain’t eBay.

Started real simple. Just typed “HHI Beach and Tennis Resort” into Google. Like an idiot. Got a million links, mostly useless travel booking sites showing me rooms. Totally pointless. Felt like I was searching for directions to the moon using just a magnifying glass and a local bus map. Needed a better plan.
Actually trying to figure it out
Fumbled around online forums next. Read stuff from people who supposedly bought hotels. Half of it felt like made-up stories from guys trying to sound big. Annoying. Finally stumbled on chatter suggesting the big resort hotels like this almost never pop up on regular house sale sites. Duh. Should’ve guessed that.
Made a few dumb phone calls. Called some random real estate agents near Hilton Head Island. Asked them, “Hey, you guys selling that beach resort thing?” Got mostly confused silence or quick “Nope, can’t help ya” hang-ups. One guy actually laughed before saying goodbye. Not helpful. Felt like I was calling Pizza Hut to ask about buying the Pentagon.
Finally landed on something useful: the words “commercial real estate broker”. Ding ding ding! Found a few brokers claiming to specialize in big stuff, hotels, resorts, in that South Carolina area. Started emailing. Responses were slow, like watching paint dry. Some asked for proof I wasn’t just messing around – wanted bank statements, investment history, all sorts of paperwork proof. Serious business. Sent what I had, hoping it was enough.
Dealing with the money monster
Okay, broker finally got back to me. Said they knew about the place, hinted it might be available, but… get this… the price tag was phone-number huge. We’re talking numbers I needed a calculator just to count the commas. Forget paying cash. Forget a normal home loan. This needed serious cash firepower.
Went down the rabbit hole of resort financing. Talked to my bank first. Local manager basically choked on his coffee when I told him the ballpark figure. “Sir, we loan for houses and trucks, not islands,” was the gist. Had to look into specialized lenders. Found groups who only loan money for hotels and resorts. Like a club for people playing Monopoly with real cities.
These guys wanted EVERYTHING. Business plans thicker than my arm. Market analysis showing people would actually stay there. Profit and loss statements for the next decade. My head hurt just thinking about it. Had to hire a guy who understood this stuff to even talk their language. Cost a chunk just for the consultant, before I’d borrowed a single dime!
The endless dance and the finish line
Months later, after mountains of papers and meetings that felt like dental surgery, things got sorta serious. Got access to the real info packet about the resort – the “offering memorandum”. Read it like a novel before bed. Exciting and terrifying.
Made an actual offer, through the broker. Felt like throwing darts blindfolded. Negotiated back and forth. They wanted more down payment than I hoped. Interest rate wasn’t exactly friendly either. Lawyer bills started piling up faster than dirty laundry. Contracts everywhere. Every page needed initials.
Then came the inspections. Oh boy. Teams crawling over every inch of that place for weeks. Checking pipes, roofs, tennis courts, pools, the little soaps in the bathrooms – everything! Found a laundry list of “recommendations” – which was basically fancy talk for “stuff that needs fixing, pronto”. Used some of that list to argue the price down a little more. Felt like a tiny victory.
Finally, after what felt like years of stress and paperwork thicker than the resort phonebook, we signed the final papers. Closed the deal. Sat there staring at the keys, not really believing it. Felt less like winning the lottery, more like surviving a hurricane.
What I learned the hard way
- Broker is king: Trying to find a massive resort sale solo is impossible. You need a broker who swims in that commercial real estate ocean. No way around it.
- Money isn’t just big, it’s weird: Financing a resort ain’t like getting a car loan. It’s a whole different beast with its own rules and gatekeepers. Be ready to bleed consultant fees.
- Due diligence ain’t optional: Inspecting a place that big takes forever and costs a ton, but skipping it would be like buying a used spaceship without checking the engines. Don’t even think about skipping.
- Patience is your only friend: Everything moves slow. Painfully slow. Broker replies slow. Lender approvals slow. Lawyer reviews slow. Pack your patience. Seriously.
- Expect headaches: It’s never smooth. Price negotiation is rough. Paperwork is endless. Problems pop up constantly. If you go in expecting easy, you’ll quit before lunch.
So yeah, “simple steps” it was not. It was a long, expensive, paperwork-choked marathon. Would I do it again knowing all this? Maybe. But man, would I go in expecting a different kind of battle.