Welcome to the club. I have a few local members that say a newage(bug/blob) feel more luxury and a classic is raw. As Dan says it does depend on the life the car has had. I have a UK classic on 170+K miles and have no real issues. Couple of odd bits like wheel bearing and a gearbox oil leak. Nothing catastrophic. In comparison a friend had a blob on 88ish thousand miles which went to the breaker because of ringland failure. In the options you've shown I don't think one car is more problematic than the other. Maintenance cost are basically the same. You already do bodywork so rusty rear arches won't bother you for long.
If you're local to a monthly meet area you could pop down and have a nosey over the different cars. Trust me, we will all gladly show you around. Any excuse to show them off.