What I would do, is build the '65 as a nice 289 with an overdrive, then get a heavier car with bigger weel wells and build a stroker ... oh, wait, that's what I DID do :rofl:
Here's some random thoughts from my own exeprience:
My daily driver (365 days a year in all weather) is the '66 in my sig pic. On the way to Knott's last April, I averaged 20mpg and got the best MPG in our "convoy". Then I drove it to the track 2 months ago, and without even tunning it up, ran 14.1's and 14.2's all day, beating many 302's and a few 351w's (and got beat by Daveoxides 351w by .02 seconds). Why can't I run in the 13's? Because I can't fit enough tire in the wheel wells to get any traction.
On the other hand, I've been driving my '69 with the 408 and Tremec all this week to work to get some miles on the clutch so I can take it to the Dyno. I go 52 miles round trip and go through more than 1/4 tank a day ... taking it easy and a lot of freeway driving. Now I have traction, now I have power, and I have yet to find a road where I can put my foot to the floor for more than 10 seconds at a time. In other words, unless you live in the country, you CANNOT use all the HP of a 408 on the streets ... at least not without getting tickets or killing innocent by-standers. :lol:
Not trying to convince you one way or the other. I know I have the best of both worlds, so just wanted to share some pro's and con's of each.