Date registered: Jul 2006
Vehicle: 1999 E55, 2001 E320, 1990 560 SEC, 2004 ML350, 2001 ML55, 1995 S500, 1998 SL500, 2010 E550 Sport zoo
Location: NW Arkansas, La Jolla CA, Hong Kong
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The '99 W210 E55 is a great daily driver, the only small thing to be sensitive to is the fact of the factory lower sport suspension (spped bumps, steep driveays) and be careful with parking near curbs to avoid "wheel rash" to your sport wheels.
The only "real" maintenance costs short term are:
1) a tranny service (the original MB spec was "sealed for life" which was later changed) and actually you are right on the mielage target for a tranny pan pull and partial fluid change (note use the original correct MB spec fluid). This service costs about $350 at a MB indie. They will also check the tranny connector plu, a $20 part, and replace it if required with a better designed updated part.
2) The E55 uses a staggered tire confirguration, wider rears, and the performance tires wear quickly as compared to a standard sedan. Replacement tires run from $800-$1200 depending on brand/series. 15K - 20K miles is normal range of wear for this sport sedan. So the condition of the rubber on the car now becomes a item you should check.
3)The battery may or may not become a short term issue, depdning whether its a original battery or a replacement.
4) To keep your climate control system operating optimumly, I would recommend a AC evac/fill, which any competant AC shop can do and does not require a MB specialist, for like $80
A '99 E55 with this mileage is a rarer car, and yes that low mileage does earn a premium for the selling price, and yes this would be a great car to own.
However, edmunds.com (under the "appraise your car" feature) is a much more accurate 3rd party realistic estimate of the value of the car, rather than KBB which for a dealer tool sets selling prices higher than what is realistic, and KBB then sets trade in value lower than realistic value too - again, primarily a dealer tool.
If the car is showroom fresh, best possible condition - then private party value will come out around $11.5K, and dealer retail about $13.5K - $17K is quite pricey.
Overall, do a google for a Car and Driver test report on best used sport sedans under $25K, where they called a 1999 E55 "close to bomb proof".
If you want a reliable performance sedan, that will make a reliable daily driver, you do have the line on a very good car.
If you could wrap the deal at a more realistic price using more accurate edmunds.com value (even if you paid your friend edmunds dealer retail) especially since you plan to use the car as a daily driver rather than a weekend car, then you could become a very very happy owner.
Keep the faith !