Just my experience...
I've driven land rovers since I was 13. On the road since I was 17. Never had major problems I've not been able to fix myself (then again, only driven a year and a half).
I've got a defender 110. I can throw all my mates and party gear in it and go off wherever it takes me. Insurance was intially over £6,000 (though that was a non-specialist insurer). Now its £1,700. However, I have heard that insurance on 90s is alot cheaper.
Mines a td5 which is reasonably new (2000) and has a big engine, so insurance also will be up for that. But on the plus side I do get around 30mpg, a full tank costs around £80 from empty. So can get over 300 miles for that money.
I'd reccommend a landy to anyone looking at a first car. It teaches you that you can't race around, it simply isn't safe to do so. You're interested in it and it helps teach you about mechanical means and vehicles in general. And it can do anything. You clean it up and polish it, and you can drive it to your wedding (ask around, people do this) or a school prom. Then you can shove your mates in and go to a festival and sleep in it, and carry your mates with all the gear. Then you can go and play in a muddy field.
At the end of the day, its a perfect vehicle for anyone. I reccommend one to my friends. And so far, 3 have bought them!