Ed,
I think once you get to the $100,000 +/- category, then you can get a 360 Coupe (not a Spyder). The $50,000-$80,000 category is where you would be for a 348/355 or a Testarossa. Just ballpark ranges. A really nice GT40 will set you back about $100,000 +/- depending upon whether you perform the work or not and what your choice would be for the engine/transaxle.
Regarding the Testarossa, as all Ferrari's do, they have their own inherent issues. You should read some articles written by Michael Sheehan. He writes for Keith Martin's Sports Car Market magazine. He's written about the Testarossa as well as virtually every Ferrari.
http://www.ferraris-online.com/pages...=SCM_200607_SS
Great choices all around. I like all of them.