John, I think a 360 might be a good choice. I see you're looking for a coupe and not a spider this time. Opening up another option, is always a good idea. Now you just have to find the right deal.
sisterhood....lol....Just get an F40 and then you will have fufilled all your fantasies.....well...not all.
I think it is well documented that the passenger seat in the 355 is capable of holding larger bolt ons than any other car. The seat belt has more give and the seal back lumbar has more stiffening. The center console is also lower to promote passenger/driver interaction.
Sorry to see you didn't sell on eBay...no action until last day....just people looking for a real bargain....hold your reserve at market value, advertise in the Ferrari Letter, FerrariAds.com, and locally, since you are near a metro area. As an observer, the fact that it sounds like you don't know if it needs a Major service is a turn-off. I bought my F355 after a $8700 major....potentual customers are going to discount from the asking price! Good luck!!