if you cant work on a car yourself i really dont recommend getting an older car. A caddy will need quite a lot of attention, will probably need welding at least once. All the work will end up costing an arm and a leg at a garage.
Or are you willing to learn? Apart from the welding all maintenance and fixes needed to a caddy are pretty easily done with cheap tools and a little time. Id always be happy to offer guidance and advice on anything you needed doing ive done about 20 caddy engine conversions, built about 10 caddys from standard ones etc. I know the mk1-mk3 golf range pretty much inside out.
The other thing is with a caddy they are cramped inside, no room for great stereo stuff really unless your going to be chav about it. You cant leave anything in the back cause it WILL get stolen. Parts can be expensive for them due to "scene tax" straight tailgates are £200+ etc. Having only 2 seats WILL annoy you.
But apart from that they are cool as funk and can be made to look awesome if done right although i have seen many many wrong ones.