Since you already have a V8 and a boxer 12, a V-12 would be a nice addition.
A late 250 PF Coupe would be nice, but a 100 point car would be over your price range. Otherwise, you're probably looking at a 2+2. A 330 GT 2+2 would be a nice addition. You might be able to get into a 4-headlight 330 GT. Or, if you want to spend a little more, there is a 330 GTC at Fantasy Junction right now for $98K, looks like a decent driver.
After a bit of research, I am coming to the conclusion that either a 330 GT 2+2 SII or a 365 GT 2+2 are my best options. I will probably start a search for both models and then choose the best available in my price range.
The intended usage would be for long day or weekend trips on highways and larger country roads. The impression I am getting is that the 365 GT 2+2 would be the more comfortable car for this type of usage, but the 330 GT 2+2 S2 might be more involving to drive. One of the things I really enjoy about the 512BB - Boxer is the "raw" driving experience. :D