The only way I have done it is to put a lot of epoxy in the hosel so there is less air, and then just keep twisting back and forth as you assemble until you are sure the shaft bottoms out.

Make sure that the shaft is not obstructed. Sometimes there is old epoxy in the tip of the shaft, this has to be drilled out or pushed out with a ramrod.

Stick a tee through the grip end of the club, a hole in the grip tape won't hurt anything. Just be mindful when cleaning the grips.

Hi,
When you want to glue head on shaft, you must consider some things before:
- if shaft is new and no grip installed, it is the easiest one. Put some epoxy one the shaft and some in the head. You do not have to put to much. When you place the head on shaft, just turn the head to assembly the head. The extra epoxy will find a place inside the bottom of shaft and the air will pass through the shaft.
- if you install the head on a used shaft having a grip. You must prepare the shaft and use a drill to remove epoxy blocking the bottom of shaft. Also, if the grip is installed, make a hole passing in the center of the top cap of grip trough the tape under the grip. Air will be able to pass. And then you will be able to install the head on the shaft.

If you try to install the head on a used shaft that you do not pass the drill through the old epoxy, the air will always put a pressure that will remove the head.
Conclusion, the air must exit through the the shaft and through the tape at top of grip.

Need to clarify. Steel shafts are hollow so the air will pass through with no problem unless the grip vent hole is plugged (assuming the grip is already installed). Graphite shafts have a solid tip so there is no air relief when assembling to the head. That is where I learned to load up the hosel with epoxy to eliminate as much air as possible, and then wipe away the excess epoxy once the shaft is fully inserted. It's a bit messy and wastes a little epoxy, but so far it works best for me.

New shafts are not a problem. Graphite or steel there is hollow in tips. In graphite shaft, tips are not full in graphite ( they like a small tube tapered), there is also a hollow. You can see through the butt’s hole to the tip’s hole.

Problems occurred on shafts that are not brand new. If you removed a shaft from a head, there is epoxy that will stay in the hollow of the tip and air could not pass.
Before reinstalling this shaft on another head, you need to to drill in the tip to remove the old epoxy and the air will be able to go through. There is a special tool, like a chuck that you attach to the shaft’s tip and you could drill in the middle. This is the way that you will only drill the old epoxy.

If you put weight in the hole of the shaft’s tip ( to adjust swing weight), there is a small hole in the weight permitting the air to pass trough.
I hope my explanation are more easy to understand this process.