I've recently acquired enough money to buy an old Land Rover discovery. I have seen 2 that caught my eye on Craigslist. One is a 2003 with 150,000 miles. One is a 1998 with 44,000 miles and with a brush guard and top rack. Should I go for the newer one, or the older one with less miles

 

Personally, i would go with the 98 with 44000 miles. I own a 2003 and got it with 101000 miles, and am happy with it. But low mileage, and some TLC, you could have a long term relationship.

 

Buyer beware slogan comes to my simple mind. Is there adequate documentation to support the seller's low mileage claim?

150,000 miles is getting up there but shouldn't be a deal breaker, if well maintained and in excellent condition could be a much better choice than one with fewer miles in lesser condition.

'03s have had a questionable engine reputation and are CDL deficient. Resale value may enter equation if purchase doesn't work out for you.

If your your first LR/Discovery purchase you'd be wise to do much web searching prior to a purchase. If not scared off by many reported maintenance issues you may want to focus your attention on the advantages/recommendations of different years of same model. Plan on spending money in the future for upkeep.

If possible keep money in pocket until the right one comes along. If one those two you mentioned meet your standards go for it.
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go with the D1 it only has 30% of the electronics as the dII