Do you want to be bankrupt when it breaks or reaaaaallly bankrupt?
E39's have a long list of problems and are pretty expensive to maintain in the long-run. If you go that route make sure you get one thats been well cared. Be wary of any "bargains" you may run across.
I don't know too much about the E60's admittedly but I have blown one up at the BMW Performance Driving school. They are wicked no doubt... that V10 is still one of my favorite sounding engines. The E60 M5 was just a strange car in the sense that's a big heavy saloon with a high hp, low torque engine... not exactly the recipe for a good daily driver. Another thing to think about is that the E60 M5 has a small gas tank and gets about 14mpg when you're being nice to it so you'll be spending a lot of time at the pump.
Can't go wrong with either if you're willing to dish out the cash for them.
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1997 M3 Coupe - BMWCCA I-Prepared #22
2006 M Roadster - 23,000 miles and slowly counting
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