We did the trip from the West Coast to the East Coast. We took our time. San Diego to Florida took us 5 years. We have fuel for a 2000+ mile range but you can do it easily with a range of 750 miles including a reserve and generator run time. We ran the coast and our longest passage was just over 48 hours with maybe 12 over-nighters and the rest day hops. Morgan (ak the Captain) likes to get to shore a couple of times a day if possible.
If you need to go back to the states or do land travel, there are many places that you can securely leave the boat. Seasonal weather is a consideration but with a little planning it can be a pleasant ride. The two areas on the West Coast you need to pay attention to are the Popaguyos off of Costa Rico and the Golf of Tehuantepec between Mexico and Guatemala. The winds can be near hurricane force but with today's weather forecasting, the winds are easy to avoid.
A couple of very good cruising guides for the trip are written by Eric Baicy/Sherrell Watson and Captain Pat Rains.
Cruising Guidebooks For Central America | Always Up-to-date
It's a trip we highly recommend. The people, culture, food and history is not to be missed.
EDIT: You can get all the above cruising guides for les than $100. They both talk about seasons, fuel, stops weather etc. There are also 2 Yahoo groups that have information about the areas you'll be passing through.
More EDIT: Bob and Elaine on Mar Azul, a Defever 44 did the Caribbean loop which included Panama to FL. Here's their link: