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Go for an 80's 911
I think you'll find the prices on late 60's and early 70's 911's out of sight. The early 911's have really been appreciating a lot over the last few years. That makes it a lot harder to find a good buy. Looking at these early cars you may want to consider a 912 - 4 cylinder instead of 6, but still fun. I don't believe that the ridiculous appreciation has caught up to the 912's yet. I've got a '72 914 that's very "raw" and great fun to drive, so that's something else to consider, just be smart as there are a lot of junker, rust bucket 914's out there.
If my heart was set on a 911 though I'd steer more towards the 1980's cars. They're relatively cheap now and are due to appreciate in the future. I know it's not an investment, but an 80's vintage 911 is probably going to represent the best "deal" for you.
Kirk
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2000 Boxster S - Gemballa body kit, GT3 front bumper, JRZ coilovers, lower stress bars
2003 911 Carrera 4S - TechArt body kit, TechArt coilovers, HRE wheels
1986 911 Carrera Targa - 3.2L, Euro pistons, 964 cams, steel slant nose widebody
1975 911S Targa - undergoing a full restoration and engine rebuild
Also In The Garage - '66 912, '69 912, '72 914 Chalon wide body, '73 914
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