Which is better in the military, living ashore or on a cutter?

It all depends on which branch you select, their rules and where you are stationed.  Your question assumes you will be going into the Navy.............the Marines - you could be stationed to either while in the Army or Air Force - you will NEVER be stationed on a ship.

Personally, I would rather live on dry land. I hated being stuck on the "Floating Prison."

Even though, I was in the Navy, but I was a "Sand Sailor." 

Do you know what a Cutter is??   A small sail boat.

There is no way you could live on a Cutter for any length of time.

What Branch of the Military??   Army, Navy, Air Force, Marines, Coast Guard??

Where are you going to be stationed.  Alaska for instance.  Living on a small sail boat in Alaska would be interesting.  

Anonymous, you sound like my dad. 

Is he still available now I can cross the border

That’s entirely a personal preference, Mark. But you need to be careful that you don’t get suckered into some rip off deal at a shady car dealership. Because you are a car salesman‘s wet dream.  I mean that you are extremely gullible and would easily be manipulated into a really bad deal.