I'm actually quite content with what I have , but if ( from the half dozen times a year I do it ) the lottery dropped a bucket of cash in my lap , then I'd fancy the following .
W113 230SL Automatic
Ponton 220S Cabriolet
W111 280SE 3.5 Cabriolet
W109 300SEL 6.3
W116 450SEL 6.9
W107 450SLC 5.0
R107 500SL
R129 SL600
Oh , for use in winter
300TE 4-Matic
Any older air-cooled Beetle with 12V electrics .
And for nostalgia
W110 190
W115 220/8 with manual column change ( the car I learned to drive on ) .
Of course , if I ever became obscenely , filthy rich ( it won't happen ) then I'd have something like an S , SS , SSK or SSKL , maybe a 540K Special Roadster and something Veteran from the dawn of motoring like a Mercedes 60 or a 90 as campaigned in the early road races . Since I would not need to work , I'd spend my time participating in events like 'Classic Days' touring the world's nicest scenery in the world's nicest cars