Advice & direction...

In general, yes, you are too old to get into an entry level position. You may pull it off though with a good look, great personality, excellent service and organizational skills. Floral skills? Table setting art? Silver Service? Cooking? Ask yourself, "What can I bring to the table?". Where do you see yourself fitting in? How physically fit are you? I don't mean in looks, I mean in endurance and ability... Working on a busy charter boat is like a marathon, sometimes 18 hr days 7 days a week for weeks and even months straight. It can be wearing.... Private family boats are better typically, lot less stress and often friendlier to crew with some "mileage"

You know, thinking about it, there are a lot of mid sized US Flagged family boats that hang out in the summer between St Augustine FL and Norfolk VA, as well as up in the Long Island Sound in the summer that may prove to provide you more opportunity that Ft Lauderdale at this moment. I'm here on my vacation right now, and things are a bit slow, but my friend who is a crew agent is doing slow but steady business. You might find something, but then you might not find anything in a year. If you are in a position where you can take a year off and give it a go for a year with about a 30% chance of success at gainful employment and about a 90% chance of having a good time away from the rat race, go for it. If you "need" to have a job by years end, well, if you don't have one by fourth of July weekend, perhaps you should put out your feelers in another direction. STCW is pretty much a requirement. Check with the Community Colleges, OCC in Newport Beach probably has it at a very reasonable rate and can get you a deal on a hotel room. SDCC may have something as well.

Also, if you know how to sail, may as well go for that market because you have added value there.

I'm a former OBcian and resident of Rock-n-Roll off Shelter Island....

What's at the Shelter Island docks these days?

What we have on this coast that you don't is boats behind houses. Think about So Florida as 100+ miles of Coronado Cays. The marinas you are used to where all the boats are berthed enmass by the thousands don't really exist here. The biggest factor working against you is that the market sector where you are most likely to find a position on board is also the market sector that has been hardest hit by this economy, which is the 65'-120' boats running a US flag.

Entry level day working... that's no way for an adult to live.

Day workers live in crew houses, typically sharing a bedroom with 1 other person in a 4 person, 2 bedroom house with kitchen. Last time I went that way a few years ago, it was $150/week. Can be a good way to go. There are also cheaper accommodations in bunk rooms with 4-6 in a bedroom and an apartment complex full of the same like Flloyds, and places like The Bridge across the street here that have from private rooms to bunk rooms. You'll be coming in off season so good chance you can get individual use of a bunk room, and all rates will be down some. The two major providers of housing are going to be Smart Moves and Nautilus Group. Nautilus Group also runs a web board that has a Dayworker listing. You'll see most of the independent crew houses advertised as you visit the crew agents on their bulletin boards. You need to find a crew house that meets your attitude. Some places are quiet with mostly over 35 crew, and some it's the 18-24 crowd and it is going off at all times of the day and night. With the market the way it is and when you want to show up, you may be able to find a private condo to rent furnished with no lease, expect to pay around $750-$950 a month with a first/last/deposit to move in. One advantage you get doing your STCW-95 here is the networking opportunity and the contacts you get through the school.

To get your feet wet in your own backyard, go apply at Hornblower or Harbor Excurions.

I'm sorry, I meant Neptune Group. You can try France or Mallorca, but your chances of success are lower than here. With US flag boats you eliminate a good bit of your competition because they are supposed to hire Americans, or at least green card holders.

That brings back memories, I used to work Invader back when she still had trees for masts. RIP Larry Briggs LOL, there was an interesting character.

The odds of you earning a living as crew in this economy and at your age is between zero and none. It's real hard for a captain your age to get work. However, maybe a way in would be through the back door. Your experience could serve you well selling boats. Boat salespeople are starving like everyone else right now, but it will eventually pick up. If you sell them you will be making connections that could get you on board at least enough to see if it's for you.

Another avenue would be to check out findacrew.net, crewfinder or crewnet. They are free to join and the first two have some entry positions that do not require qualifications. Crewnet have a local office in SD.