My best mate is really REALLY into old cars.
His first car (25+ years ago) was a Morris Minor and it was old then.
He kept this car on the road for many many years. To the best of my knowledge it broke down once. This car was restored by him. Upgraded by him (It ended up with a 2.0 litre Fiat Twin Cam engine, 5 speed box, Ford 1600 running gear) and it used to go like F@ck but looked stock as a rock from the outside. It used to stop and handle as well.
He ONLY has "old" cars, currently he owns a MkI Escort estate and a Reliant Schmitar both are in very very good condition. He's only just recently got rid of a 1959 Morris Minor again, "improved"
If you're going to buy and run an old car you are going to have to work at it if it is going to be your daily drive. If you try and treat it like a "new" car then you will, sooner or later get caught out.
You are going to have to learn about cars, buy TOOLS and get your hands dirty.
The Massive advantages of having an old car are:-
You really can work on them
Parts are usually cheap
Even if you put them into a garage the bill shouldn't be too much cause you can use a local garage rather than a main dealer
The are Soooo Cool
NO ROAD TAX!!!!! This alone is worth getting an old car
If you buy a good one then there won't be any depreciation, in fact you may even make money or at the very least have "free motoring" excluding wear and tear
Advice for buying a classic car:-
Do your research
Join the owners club (sad but very very good advice)
BUY THE BEST ONE YOU CAN AFFORD There is no such thing as a cheap old car, it's just a car you haven't spent a lot of money on YET!!!!
Go to car shows
Look at the magazines (Classic car is a good one) see the parts availability
See what people around you are driving. If there's a healthy VW Beetle scene for example look at Beetles you will still be in a minority
Have you got somewhere to work on the car IN THE DRY there is NOTHING repeat NOTHING as soul destroying as working on a car in the cold and P!55ing down rain knowing you HAVE TO GET IT GOING FOR MONDAY
I'm also into old cars too, so my views maybe a little bit biased. AND I'm in the lucky position of "having my mate" wanting to do up my 1961 VW Beetle