D2 S8 for me. Listen to your heart, not your head - life's too short for that! 
Why? If you find a good one with low miles and/or a gearbox service history and look after it, then it should be OK for a good few miles. Even if it does die, you can get a remanufactured box from a reputable company like Mackies for much ls than £3.5K and it'll be better than new. That'll give you another few trips around the clock if you have it serviced properly.
And then there's the rarity value and that classic styling. As well as indications that they will increase in value soon.
The D3s are very nice, I agree, and having sat in Tonupkid's S8 at the weekend, I was tempted. But, in the end, this is a very personal opinion. However, you must have listened to your heart to want an S8 in the first place, so keep listening! 
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2002 Final Edition S8. Ebony black with Silver Grey leather and myrtle wood trim. Current mods: solar sun roof, 20mm rear spacers, 15 mm on front, red brembo callipers, 6k headlights, rear view camera, engine remap, alloy dash dial rings, alloy navi rings, tt/phaeton pedal upgrade, (and custom matching foot rest) dension ipod interface & parrot hands free kit (both fully hidden), av input, tv in motion switched thro' PF switch in blanking plug right of steering column, Audi 'quattro' sill covers, repositioned centre console switches, radio clock, .
Planned mods: auto-dimming rear view mirror, dash cam (as steamship's), fit the ski hatch, refit philips drl's (or maybe not - nope, definitely not - horrible botch!).
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