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Owned E39 M5 for 6.5yrs, and now have owned E90 M3 MT ZCP for 3.5yrs.
Driving-wise, they are very different in character. The E39 is like a luxury car with a beastly engine and surprisingly athletic handling, while the E90 is a 997 C2S competitor but with 4 doors. M3 is much more athletic while M5 is more of a burly muscle car. Both a lot of fun. I'd say the M3 is the better driving car overall but the M5 has a certain character and subtle swagger that is hard to resist.
Ownership-wise, you basically choose between endless mild-moderate problems with the E39 vs. less common but more serious problems with the E90. I got around the latter with a warranty, and will do rod bearings if I keep the car past warranty. For the record, my M3 is now about the same age in years/miles as the M5 was when I got it. M5 has a lot better highway range with a bigger tank and about 4mpg more.
Interior/trunk size is pretty similar, the E90 is mainly just narrower. E39 has some parts that feel richer (mine had leather everything incl glovebox door, sun visors, dash) but other parts are far flimsier.
Overall I'd say I like driving the E90 more, but I had a closer connection with the E39. M3 is a more satisfying performance car but the E39 has more character and soul to it IMO.
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