Hi Baker, On our last boat, there was no device used except for the S/S clamshell-cover on the outside. (To deflect the bow-wave water away from the hole). I don't have access to that boat now (sorry, it left NC about 4 months ago for a year-long+ cruise/Great-Loop).
The best I remember, the hole was about 3/8" in diameter and had a copper tube, form-fitted and flared on both the inside and outside; it was likely epoxied in place, but I don't know for sure.
I don't know how they drilled the hole, but I would guess they used a 'jig' that accommodated the angles; and it was likely drilled from the outside-to-inside. (Careful measurements). (One of my buddies has a portable 'jig' that accommodates drilling angles, using a standard hand-drill; I've seen them for sale at specialty tool companies)...
The bow on that boat was/is solid fiberglass; no coring. So I don't know if the sleeve was necessary; could have just epoxied...
On our boat before that one, there was just a hole; again about 3/8" best I remember. There was no sleeve and the there was no Clamshell cover. Using a small artist brush, I 'painted' the hole with West System epoxy, and added my own Clamshell-cover....