57/58 plate E class will be the facelift W211 model, which is a very good model, don't be tempted to a pre facelift though.
Generally those large German cars such as S class arn't especially trouble free and problems with them are often beyond the average garage so a specialist indy it is, which is fine but do you have one within easy reach.
I notice your friend currently has a 52 plate car, cars from the sweet design period of the 90's are among the best ever made, those designed 10 years later were heavily laded with electronics which can give problems, ie 430 Lexus isn't enjoying the same reputation as unbreakable that LS400 did.
Just to put things in perspective, an air sprung Mercedes SL/CL front shock absorber can cost well over £1000 for the part alone, some of them the bottom ball joint is part of the shock hence work out how much 2 worn ball joints could cost.
He's also doing the right thing buying properly looked after cars, he probably does a lot of his own maintenance too, this is the real cost saver.
Unfortunate that you had the Skoda written off, the quite normal work you list on the car could be required on all cars, its just unfortunate that the cambelts on such cars are such a time consuming job when the vehicle is designed to be manufactured with scarcely a thought about long term ownership, in comparison my new (55 plate) Landcruiser i shall change the cambelt on next week, £72 for a full Gates kit and approx one hour to do, all cars should be designed to be maintained.
If you want a luxury car around the 57/58 plate years, then you could do worse than find a well looked after W211 E220 Merc, but i'd also look at Lexus IS250 or GS300, i'd rather put my faith (and me hard earned) in a proper Japanese car of this type than anything German.
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