OK, I'd need a much bigger win than 100G before I could allocate that much to wheels. Assuming I could I'd go as follows:
GTA LeMans
A110-1600 (prefer 's')
Original Lotus Elan Sprint
Espace V6
Clio 182
Audi RS6
+ the revolver... all the cars I fancy trying for a little while, Starting with A Lotus Europa S2, I'd probably move on to a larger one after like a Jensen Interceptor or a Aston V8 then back to a little one like a Matra D'jet or a porker 914/6 etc...
I would never ever buy a new car (I hate paying the taxman the duty) and would change the clio (city run-about) and Audi (country run-about) on a regular basis.
This lot probably leaves me change but 'the revolver' would bounce the finances up to that level now and then (is there such a thing as a cheap dino 246?).
Alpine A110, Renault Safrane 2.5dt, Hudson Kindred Spirit (Renault powered), transAlp (Honda) and Ducati Multistrada