I am pretty happy with my current fleet of MBs, but I guess if I had the additional income, I would step up each model in such fashion:

ML320 for an ML55
300E for an E55
500SL for an SL73

And maybe throw in an S500 just for grins...and get Norm Abrams over to expand my garage space!

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2009 ML350 (106K) - Family vehicle
2001 CLK430 Cabriolet (80K) - Wife's car
2005 BMW 645CI (138K) - My daily driver
2016 Mustang (32K) - Daughter's car