As a vet of many such trips as well, I'd say you have already received great advice. My only $.02 to add is wait until April if possible, as the likelihood of settled weather in April and May is significantly better. However, trying to get a congruence of daylight, fair weather, benign bar crossings, ports of refuge, a route to avoid crab pots, etc. most of the time is not simple, and bears some serious thinking and planning. But the trip's been done many, many times by many, many boaters in many, many boats. It's perfectly doable, with care.
For what it's worth, i'm not a fan of weather routers. They are seldom local, and it's local knowledge that dominates most everywhere but open sea. Talk to the fishermen and charter boat captains in each port, and follow their lead.
Regards,
Pete