Can a retired Airman own a yacht?

I'd go for the bass boat and the home. If you can do that and save enough to buy that yacht in 10 years, you might be able to afford the upkeep (given what your skills may save you). You can easily spend upwards of $100K a year on that size boat, especially if you actually cruise. Maybe you'll even eventually sell the home and retire onto it. Plus, you could well be dead in 10 years. Dreams are wonderful, but they're no substitute for enjoying today.

P.S. The bass boats are more fun and you'll use them a lot more than you will any yacht.

P.S. Given that you have to work and your skill set, why not work to become a captain. For the past almost 30 years I've gotten to cruise way more boats than any owner, didn't have to pay the bills, and made a decent living. Now, after almost 60 years total on boats I won't mind if I never set foot on a deck again.

Your plan may make sense. Yacht implies different things to different people. However, you can get some very decent liveaboard boats in the 40-50' range for a reasonable price. Nycap says to become a captain. Well, there are other things to do. Use the 10 years to learn more about boat engines and doing mechanical work on them. Start with basic STCW for you and your wife and try to get deck and/or interior jobs on boats to allow you to build sea time and enjoy.

The fact you have a lot of mechanical and electric skills will aid you in doing some work yourself and saving money.

Now, the other word of advice is purchase within your budget for initial expenditure and for annual costs and maintenance. If that means a bass boat, fine, although I have seen bass boats which sold for what you could purchase an older cruising boat. If it means 30' instead of 50', then fine. Smaller boats will get you on the water and while they may be a bit cramped with a military background I don't imagine that would be something you couldn't tolerate.

You're thinking of this well in advance so time will help you figure it out. However, I won't discourage you from the possibility of owning a boat of some size other than a bass boat. Some may depend on where the two of you locate.

Is your wife also military? Or will she be ready for retirement when you are ready for your second retirement? You don't need to disclose here, but a missing piece of the equation is her monthly income at the time you get ready to do this.

Then back to the boat. There are a lot of retired military people I know who have become trawler owners. They're interested in minimizing their annual costs, including fuel and dockage. Others have chosen cruising boats that are neither yacht nor trawler, such as Bayliners, or by the time you get ready perhaps Meridian, boats that can be obtained at very modest prices and are fine for coastal cruising, just not for crossing oceans, but then few people ever cross oceans.

Continue to follow and think and then you'll see over time where it will lead.

Similar to Searay perhaps but not an express boat as they are. Instead something with more usable space and probably a flybridge.

When I hang up my hat in a few years and take it easy after what will be close to 40 yrs of making my living from my involvement with things that go to sea I will buy a boat myself.

After seeing so much and being on such fine vessels I will buy a very good quality maybe custom made 5 or 5.5m Aluminium runabout with a high standard of outfit in regard to functionality and safety , it will live on a trailer in my garage and be powered by a 4 stroke outboard. I will take it out and use it as and when I want and when finished bring it home , clean the fish, open some scallops if I have some then put it away after a washdown and go in the house have a shower, a few beers and sit on the porch looking at the cows in the back paddock as the sun goes down or on the other side of the house if it is coming up.

I have previously looked at a larger motor boat, the lack of a decent place to keep it and the difficulty of moving it from the east to west coast if the wind is in the wrong direction when I want to fish or just go for a hoon in it soon showed me the best way forward for my situation.

There are plenty of moderately priced boats that will run the area you're talking about quite well. Some with excellent layouts and plenty of room to live comfortably. There are many others doing exactly what you're talking about in that area.

Used boats can be very expensive to maintain, upgrade and repair.
Buy the smallest boat you can live with (on)
My boats keep getting smaller as my checking account gets bigger.
On a fixed income and without a rich uncle pushing 100 years of age with you as the only heir, you need to be very careful buying a big boat.
Been there, done that.

Truer words have never been spoken.

Well, we love the Exumas and all the Bahamas, but that doesn't mean we don't still love Key West.

Love Key West too, but last time we were anchored there my liver sent up a white flag and wanted to divorce me.

Say hello to Okinawa and the girls hanging out next to the main gate; They always greet you with "Hello Sailor".
Cute little things.

Car? Did you actually say "Car?" No, we'd never do that. We've been to Key West 9 or 10 times in the past three years but never by car. Next you'll be suggesting one should go to Bimini or Cat Cay by car. Of course, we don't go to Miami or West Palm by car very often. Perhaps one out of every 25 trips.