In a very similar position - me and mrs Toby only, she wants a soft top sports car that she can just drive and not worry about starting in the morning (aka she loves my very heavily modified MG Midget) and wants something that drives as well, looks fantastic and has practical touches like a boot!
So far the 350z in the GT guise is winning - last years model comes in at about 27k before trade in, cheap to maintain (Nissan!), looks good although the boot is a little on the small side.
Off to 911-Virgins this morning to look at Boxsters and older 911's; I have driven loads of them and know how good they are but also know how expensive the services will be...
Audi TT is the other choice but I think that there are far to many of them on the road and dont really stand out.
The S2000 would have been a natural choice other than I am 6'4" and its a bit of a squeeze to get in
Much as I would love another classic its her car and thus it needs to work all the time! Will be watching this thread with interest