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.