2.66 low gear vs close ratio

I'll add a comment: vntd is in central NC in the low foothills; a 3.09 won't get as much use unless he is driving in town a lot. A 2.66 will be a lot more useful roaring around the southern Appalachians; finding the right gear in sharp hairpins turns requires a useful 1st from time to time, and the 3.09 is not it. So, vnted, I would look at your intended driving terrain; if in Greensboro a lot in stop and go traffic, or never in the Blue Ridge, then 3.09. If not, and you go roaring around up towards Patrick and west of Wilkesboro up into the Blue Ridge, then 2.66 fer sure.

The OD box is just a 3 speed and having raced one for while (actually a 4 speed with too high a rear gear, which made 4th about useless), they really are limiting. You'll always find some corners needing a gear and RPM combo that you don't have with 3 gears. Same for the Passon 4 speed OD mentioned. The OD is for interstate cruising and is nice there, but is a real compromise in hard driving.

This is correct, I missed the location information.

You can almost never have too many ratios. With the OD box and the GV, there are seven usable ratios; 3.09-2.41-1.67-1.30-1.0-.78-.57. Unfortunately you cannot downshift into any GV ratio. Or more correctly, during the downshift you cannot be putting power through the box. So that won't work for roadwork. Which is why, after a rebuild, I don't use it any more.
It's hard to beat a regular 5 speed. Or even a 6 with an SBM.