Welcome aboard the TF, Doug, and congratulations on your new-to-you GB 46. A great cruising boat!
With an unfamiliar boat, you're right to prefer to work up to overnight passages outside of protected waters. For crossing the Big Bend, there are few convenient places to put in under the best of circumstances. Hurricane Helene having recently chewed up the west coast of Florida, the present circumstances are far from favorable. I think you ought to plan on making the jump from Carrabelle to the Anclote River entrance, which as you note will be about a 23 hour run as the seagull flies. If you prefer to deviate further inshore and ignore the rhumb line course, you can maintain a distance of 12 or 14 miles away from land. But given the sparseness of shoreside resources, the near shore "dogleg" route probably offers only psychological comfort, rather than any practical advantage. Another argument in favor of the direct route is that you may be less likely to encounter the floating debris that are typically carried out of the passes and river entrances after a major storm.
I'd come out of East Pass, between St. George Island and Dog Island, make my course straight to the north end of St. Joseph Sound, and enter the ICW there. On that route you'll never be out of reach of Coast Guard Station Yankeetown, in case of real need. Wait for a calm weather window, leave Carrabelle in daylight, run overnight and arrive off the north end of Anclote mid-morning or later the next day, so as to avoid searching for markers with the sunlight in your windscreen. On that subject, as Peter noted above, aids to navigation all up and down the west coast of Florida are suspect. (Parts of the east coast aren't much better). Fixed aids are often damaged or just plain MIA, and you should assume that any surviving floating aids are likely off station. Even the Tampa Bay Pilots have been reduced to daylight-only operations, owing to the ATN situation. The Coast Guard's ATN Team is out there doing their best, but it's going to be awhile.
Once you're ready to resume your trip south, my suggestion would be to go outside again all the way to the Sanibel Lighthouse and the entrance to San Carlos Bay, for the same reasons as above.
