Here is my 2 cents:

You can get a current gen 7 series Bimmer 02/03 for mid twenties.
The E39 M5 is losing its panache because of their availability and current affordability but nice cars, nevertheless.

Your Benz choices are great and will hold their value.

Jag S Type R: Incredibly classy car and a sleeper for sure.
Nice amenities and comfort and the speed is there if you need it.
I currently own a 4.2 V8 S Type and I love it. My only complaint is that, at least the standard S Type's, are plagued with small problems that can get kind of bothersome, to say the least however, Im currently looking to upgrade to an S Type R as well.