Been in your shoes, man.
Before the kingpins and some other worn-out front end pieces were replaced on the Tudor, I was also questioning whether to trailer or drive to far away spots. However, after having the front end and brakes redone, the car drives so beautifully (it just glides over the road), it's a "no-brainer": Drive it!
Suggestion- If you can get hooked up with that club, request to ride along on one of their tours and see what a well maintained A is like.
Been on several long trips, and it's such a joy (except when it's really hot). Only time it was ever on the side of the road was when the "mono fuse" blew and it killed the ignition. Found it, replaced the fuse, and away we went. To rectify that, I have since fused everything on the car separately. End of problem.
These cars are so well built, and so amazingly sturdy, I seriously doubt a properly maintained car would be any more trouble than a well maintained modern car. But then again, I'm also a bit of a noob too, so we shall see.
Very best of luck to you!