I have been looking at RR and Discovery's for awhile now. I am really leaning towards a RR but I have no clue which year to focus on. I know they'll all need maintenance and have their reliability issues. I am ok with that. I would use it primarily for the trails and occasionally on the streets. Is there a better year or style to look for that is better than the rest?

 

i would suggest keeping away from the Boshe and look for a late model Gems 4.0/4.6 jmho

 

Someone once told me "if you can't afford top buy a new land rover, you can't afford to buy an old one" this has proved true for me myself. Had a 1999 land rover range rover and had issues with it constantly. Got a sport and had next to none. The newer the better I'd say. Depends on your budget too .If you can afford it get something no more than 8 years old

 

It is a matter of preference. Early Discos are a matter of fact truck. Utility vehicle has all you need for trails and road, just not as comfortable. Range Rover, not as utilitarian but more than capable and very comfortable. Drive them, check history and decide what you feel comfortable with. Yes, all can have problems, but what used vehicle doesn't.

 

Yep, D1 is my pick. Cheap to buy, cheap for parts and simple old tech to work on.
Set of decent rubber and a 2" lift will get you any where you will want to go.

 

Stay away from 03-05 L322 with BMW engine - I had one, tons of engine-related issues. Extremely well documented in all Range Rover forums. The best forum for Range Rovers is RANGEROVERS.NET HOME Lots of them for sale on the market, cheap, and therefore very tempting for first-time RR buyers. But consider the cost of the vehicle to be the membership price to a very expensive club. If you do not have the time, experience, tools and motivation to fix everything yourself, you're going to probably pay thousands of dollars in repairs very soon after you buy it. Also try to stay away from the 06 - First year of Jag engine, so more issues than later years. Same as any new model of any car - first year has a few issues. Also, the 06 still has the really poor quality interior. My vote would be an 07 or 08 Supercharged, although these have not dropped in price very much within the last year or so. Cheap gas probably has something to do with this. The Supercharged models are nice because they also have the rear locker as standard, which is a must if you want to do some serious off-roading.