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I've owned a 2000S for the last 5 1/2 years and the car is a blast. Besides the S, I have two data points for you to consider:
1. Picked up a '98 (117K miles) in Sept. 2011 for $4800. 2 Owner car with decent, but not complete maintenance records. The top was shot and would not go up or down automatically. Overall the car looked good with very few dings or paint chips but was very dirty. The PO had his work done at a reputable indy but the labor was killing him. When the top quit working and the window split, he'd had enough.
I ended up with about $6800 in the car, bringing all maintenace up to date and fixing the power top (and replacing the top/frame). I did the labor. The car cleaned up very nice and ran great. I put about 1000 miles on it while I had it. I sold it for $8200 in October of 2011. The new owner has had no problems with the car since its purchase. It is not a daily driver.
Bought another 98 in Sept. of 2012 for $5,400 (117K miles again). Two owner car and the roof worked but the back window looked like crap. I ended up with $7900 in the car, mostly on new top with glass, replacing the seats and suspension and brake work. I put 3000 miles on the car while I owned it and worked on it. I sold the car to a friend for $7700 just last month. It will not be a daily driver, just a toy to cruise the beach.
The key is doing the work yourself. Neither of the cars would have been worth it at all if I'd have had to pay someone to do the repairs and maintenance I did. I would have easily been over $10K in each of the cars.
Although my S has been great, there is no way I'd have kept it if I was running to mechanic for all my repairs. As an example, rear wheel bearing R/R will run you 4 to 5 hundred dollars a side at an indy. The bearing is under $50 if you do the work.
CV boots split. The boot kits are ~$10 each, so $40 for both axles. An earlier reply listed $1000 for the work at an indy. You get the idea!
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