Gil, here's a few other thoughts...
Bridge heights on the ICW will not be a problem for you at 60'...but you don't have the time for the ICW. You're timing is lucky since you'll be working with maximum daylight, and you stand a chance (never any promises from Mother Nature...) of enjoying much stable wx. Your primary wx concern will be convective activity.You must run down Hawk's Channel from Miami to Vaca Key and Marathon to transit the 7 Mile Bridge and cross into Florida Bay. Prevailing winds up into the Carolinas from Florida are SE but in the summer are light; along the coast, you'll be more affected by the day/night cycle - inland heating and onshore breezes in the afternoon, inland cooling and offshore winds at night. Any distance offshore, these effects will be minimal but you'll notice this e.g. if hugging the FL coast to avoid the Stream.Personally, I think the run sounds like good fun...but regrettably not possible in your 3 weeks. I too thought of grabbing a deadhead run back to Alachua (and Hunter wouldn't be your only option; Island Packet, Catalina, Searay all have huge FL mfg. operations) but...you could consider using that plan as a fallback and seeing how far you can move the boat in the time window you have, trucking it the balance of the distance. And don't forget Plan C: cover the distance you can and, if you get into FL, run the boat incrementally over some extended weekends to finish up the trip.The 48' RR bridge near Port Mayaca's Lock on the Okeechobee is too narrow for you to have the Indiantown Marina boys lean you over, I think...and that's a lot of leaning. Otherwise the O. Waterway would save you a great deal of time. If you were moving the boat on weekends near the end of the run, unstepping the mast in Indiantown would be a good plan; restep at Glades on Ft. Myer's Calooshahatchee but mind your crossing of the Lake with the spar on deck; it can be very choppy in wind.I make the logical offshore run, with legs into/out of all-weather ports, at roughly 1800-2000 NM (depending on how many stops and how far off the rhumb line you need to go, e.g. when crossing Royal Sound into Hilton Head and back out). The legs are defined by all-wx harbors like Atlantic City, Ocean City, Little River, Beaufort NC, Cape Fear River, Charleston, Hilton Head, St. Mary's River, etc. Fetch some small scale charts and you can break down the run into obvious legs. (I appreciate your concern about Hatteras but I'd wait to see what the f'cast looked like when sitting at a marina just inside the C. Bay entrance at Little Creek. Leaving Little Creek for Beaufort NC, outside will save you a great deal of time).Having said all this, I think you need to do the following to move the boat on her own bottom:1. Get a good cook as crew who can stay with you for the run, handle the provisioning on those brief stops (you'll be tending the engine and boat's needs).2. Tell you boss, Mate, whomever that you're sorry, you wish it weren't so, blah blah blah but you need more time for this major relocation effort and that's just the way it has to be. Offer routine check-ins by cell.3. Cover the distance you can and then arrange for the final delivery based on what makes sense from the location the boat has reached...and revel in doing something unique, challenging and fun.Or...truck it the whole way and miss out on a great adventure.Jack