No remorse here, but I’m on the opposite side of the country. I encourage you to join the association. The small price of the dues is more than repaid by the project info in members section, tool loan, MainSheet magizine (with Chic and myself) giving tech tips and interesting articles about the Catalina family. I also enjoy going to two Rendezvous a year ( US & Canada) to exchange ideas, meet and make friends. Also join the Facebook group Les

Previous owner of our 2005 boat based it out of Tampa for about 8 years- sailed all around the Keys and Bahamas. Two trips up to Rhode Island. No issues. Boat is now 13 years old. All equipment still origional except Ramarine ST60 Windex,  house & starter batteries, engine raw water pump, cutlass bearing, opening port gaskets, head hoses, anchor well thru-hull and Genoa. No leaks topside, or below the water line. We've done only limited cruising with lots of weekend stays- fuel, propane and water use have never been an issue for us.

This is the perfect boat for what you are looking to do.  I’m out the Tampa Bay Area and run the West Coast, Keys and Tortugas.  Previous owners ran Chesapeake down the east coast to the Keys and the Bahamas.

At 4.5’ the wing keel is perfect for skinny water

Ive been in some nasty weather and this boat is solid.   Ah, schedules. :)
I’d buy it again without question.
 

Bought an '05 last year, fin, dutchman, all new raymarine electronics (by me), with an ipad mirroring the chart plotter you can do everything anywhere - except engage the autopilot in windvane mode (has to be done on the P70 head unit by pressing 2 buttons). Love it.

Hull flex? We came from powerboats - nuff said. The boat is FAR more durable than we are.
Leaks? I am a maintanance person (freak?) - we have none, zero (includes green water on deck - not fun - avoid if possible!).
Fuel? we see many power boats with masts - we sail. Sometimes slow. Always enjoyable. We use 0.8 gal/hr at cruise (max) - good range for coastal work.
Still getting used to the forword head - going to turn the overhead hatch to open facing aft - natural 'fan' if you get the idea ;-)

What have you done? Something good!

Flexing of the hull ??!  I probably don't have as many miles under my keel than some on this forum, but I'll bet I've seen equivalent weather up here in the Great Lakes. I assure you, your C36 will survive better than the crew.  Every boat has its stengths and weaknesses, but for a production boat, build quality never was Catalina's problem.  I've rarely crawled into the dim recesses of my boat and thought they went cheap, as I have done with other boats.  The weakness for us is the size of the holding tank, which shouldn't be a problem for you if you venture more than 3 miles offshore.  Up here, our whole world is a no-dumping zone. 

Normal boat maintenance is required, regardless of what you sail - the ports will leak and need gasket replacements, the rigging needs to be refreshed, the diesel tank still needs to be filled, and the dishes still need to be washed.  I didn't like the production Dutchman system due to not functioning flawlessly and I still needed to haul a sail cover around, so I replaced mine with a lazy-jack and integrated bag.  It's better, but not perfect.