Slant 6 with 4 speed

For a slanty, the 2.66box is a bit of a chore with the hiway gears those cars typically have. The 2.66 works OK,until you load up the car to go camping.The 3.09 low gear is 3.09/2.66= 16.2% stronger which is the difference between 2.76s and 3.23s .
The 2.66 likes more performance oriented gears.....like up to 3.91/4.10s even, whereas the 3.09 is good down to about 3.55s/3.23s.
But when either box hits that second gear, she'll be wanting those 3.55s, for anything but a grocery-getter.
I sense you have a slanty A-body, and are looking for a little more oomph.
If an automatic, more stall goes a long way. I like a 2800 for that.
If a stick, you don't get the TM from the TC on the start-line, so your basic option is more rear gear, or a 3.09box.

But I don't advise the 3.09-od box by itself; second gear is way the heck out there. That second gear needs 3.73s just to stay even with 3.23s in the 2.66/3.09 direct 4th boxes. Criminy it's a long ways off.The OD box works well with 3.91s tho. First gear is a little deep, but they bring the second gear down to normal, and with overdrive the final-drive is down to 2.85, good for 65~2300/2400

My favorite combo is the 3.09box and 3.55s. It has plenty of starter gear, and if you stretch out first gear just a little more than you might consider normal, then it will still pull real good in second. If hiway NVH is not an issue, then 3.73s are pretty nice.
im getting ready to do this exact thing. 1975 od trans in my 198 slant duster , with factory rear I have no idea the gears in those cars but figure its 2.73 wish realm ? does that sound right ? I want the over drive as I take it on long highway trips like moparty and power tour and I think it would help a lot. are you saying its gonna be a issue here or jus that is pathetic with my rear in it ?