Just a couple corroborating/contradictory opinions to those stated above.
Lake Worth to West End is easy, especially if headed to the Abacos. We generally anchor
just south of the Lake Worth inlet the night before and leave prior to sunset. Relatively easy inlet to navigate in the dark as long as there is no dredging underway. You certainly don't want to linger at West End (now Old Bahama Bay Marina) any more than necessary due to the high fees
Jupiter Inlet has always scared me. Maybe it's a local knowledge thing, but I would certainly be very cautious about using it, especially at night or bad weather
Ft. Pierce is great, though not particularly affordable. If you can get a good deal at the municipal marina, recently renovated and expanded, that might be an option, with ocean access close by. Huge farmers market (you have to see it to believe it), and there is enough money
in town to have some pretty good talent appear at the local theater. Easy walking to all basic needs.
Melbourne has the drawback of shoaling at the entrance to Melbourne Harbor Marina, and the marina could certainly use some updating. Shame really, since it is so convenient walking to all the shops and services in the small downtown.
Cocoa Village is lots of fun with a huge number of restaurants and cafes, plenty of bars, along with the huge hardware
store, library, bakeries, etc. Only downside is there are no close by (walking distance) groceries. You are also further from ocean access.
Titusville has always seemed a little down on their luck to me. Your impression may be different. We have stayed at the Kennedy Point Yacht Club on occasion, just south of Titusville, though not much in walking distance there.
The difficulty in your situation is that easy ocean/Bahamas access does not always go hand in hand with desirable berthing locations. In addition, many areas have relatively poor cruising choices for weekend trips. You primarily will motor
down the ICW to the next port. If you want to get the sails
up and not fret over running aground it is challenging in these areas. Maybe your decision should be based on available marine
services such as Harbortown if you plan on doing a lot of work on the boat.
I am not familiar with the west coast. Hopefully someone else will chime in.