Dear George, Walt, and mid-60s Buick caregiving community,
I have no experience with the Holly SD, but a stock AFB is already tuned for the 300 and will cost a lot less!
I didn't have any luck getting an AFB rebuilt that worked very well. However, that was long before I turned to the Internet to find out who could be trusted with carburetors like the Carter AFB. I agree with Walt, the path of least resistance is to get a properly rebuilt AFB and see how the engine does with that. You can always make upgrades later.
Cheers, Edouard
P.S. I did have my Buick 300 cid engine running on an Edelbrock Performer carburetor which is a
"descendant" of the Carter AFB. The Performer is a remake of the Carter carburetor that came after the AFB but was otherwise very similar. I didn't like that carb very much either. However, my 300 engine might have already started to have problems with the valve timing and that might be why I didn't like the Performer. Otherwise it might another very reasonable choice.