With a car of E39 age group, my priorities would be good preventative maintenance and regular servicing and keeping the tin worm at bay.
The most important insurance you could have on this car would be to find that elusive first class specialist indy (finding him will be your best investment you ever make), and let him look after the car as he recommends, he will know what to look for and what to expect, he will know how to diagnose and repair at best cost, not diagnose and fit new parts as computer says till its fixed.
The most likely failure could arguably be the auto gearbox, regular oil and filter changes will prolong the life of this to astonishing mileages unless its abused, indy will know this and do it, i doubt a warranty would cover a 200k auto box refurb anyway.
I could not recommend an aftermarket warranty, with the exception of used warranties offered with makers on their approved used schemes.
Edited by gordonbennet on 21/05/2012 at 13:38
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