Have you looked at or thought about a Toyota Solara...not the coolest looking cars, but a four seat, drop top and it's a Toyota?
I started looking more into the Solara after your post. I just skipped them for looks and "Toy factor" from the outset. After looking at them more they seem less like a rag top and more like a Camry that Toyota decided to cut the top off of to get market share. They are reviewed as having soft suspension and steering and civilized power. The plan is to get a car that will slip between my motorcycle, which I am selling/trading and my Avalanche, which is fun to drive sometimes but sucks gas. The Audi, Mercedes and BMW all carry the prestige to varying degrees. The Sebring I had was comfortable and cool and got great gas mileage but broke down twice in the year I had it.
So far:
Audi - Love the cars but so many reports of mechanical issues. And one of the transmissions is legendary for needing work(and I don't know which is in what car). Even Letusbuyyourcar, who loves them, says you have to budget for maintenance. That is intimidating. I buy insurance but damned if I want to be thinking about fixing something with every paycheck that I set aside repair funds from. I think Audi is out of the running. Sadly.
Chrysler - Even my own experience was riddled with mechanical issues. And it really lacks the toy and prestige factors I want for this purchase. Sebring parked.
Any and all "Roadsters". Not for me. Tight fits, PITA entry/exit. Uncomfortable over long drives. And I WILL be taking the ragtop on the Florida vacations. Besides...I'm 52. If I got a tiny little roadster people would just think I'm having a midlife crisis. I actually bought my motorcycle as a "damn near ended my life but survived crisis". Had a heart attack and after recovering I swore I'd ride again. Well, I did. Now I want the fun of the open wind without the rain in my face, complete lack of cargo space, standing up all the time, etc, etc... So the convertible purchase is actually a step TOWARDS maturity(small step admittedly), not a retreat from it. Roadsters out.
So what's left?
BMW - I hear voices saying "No!". And my wife and I both find most BMWs boring looking to some extent. But they (like Mercedes) are legendary for both needing few repairs and costing a fortune when they do. They are soft spoken class with a touch of sportiness.
Mercedes - Best for last. And I think the fact that I feel that way is significant. I appreciate all the input and advice and I hope to get more but I think I just answered my own question by talking through the rankings. I just WANT a Mercedes. Hell, with any luck I'll have the second heart attack before it needs any repairs. LOL.