Different people will have different opinions on this, so these are just my thoughts...
If you have the time and inclination, measure the length of each bullet (from ogive to base) in a box of 100 and sort them using the standard deviation method. This article will help:
http://www.castbullet.com/shooting/standard.htm
This will give you a method to batch your bullets by bearing length in a more scientific way than just dividing them up into several lots arbitrarily.
Or, if you don't have so much time, just pick 10 bullets at random and take the average of those and don't worry about the variations in a box.
(You can also sort by weight and sub-divide your different bearing length batches into different weight batches as well, but IMO that's a bit OTT for most people).
Once you've done that, use one of the bullets which has the average measurement and keep that as your reference bullet FOR THAT LOT NUMBER! (bullet shape and length can and does change from lot to lot so make sure you repeat the process when you buy a new batch of bullets with a different lot #).
Using just this bullet, start taking your OAL measurements with your gauge. Now, the reason you don't get the same OAL measurement every time is because the measurement depends on how accurately you can determine at what point the bullet just touches the start of the rifling. This is very difficult to do with just your feel and especially with a stoney point gauge there are other factors which get in the way of that 'feel'.
Try these tips and see if you get a more consistent measurement:
Check the bullet slides smoothly in and out of the case attached to the gauge. If not, debur and chamfer and maybe use some fine sandpaper on the inside of the neck.
When you push the gauge into the chamber, the neck of the case may be constricted very slightly by the chamber, which will then increase friction between the inside of the neck and the bullet. Sometimes this can make it feel like you've hit the rifling with the bullet, but it's actually just the neck gripping the bullet. If you think this may be happening, ease the gauge out of the chamber very slightly and gently push the bullet in again until it touches the lands and then push the case back into the chamber before locking off the set screw.
The whole thing is dependent on how consistent you are with the force you use to push the bullet into the rifling. I've got more consistent results by using gravity as the force... With the rifle horizontal, put the gauge into the chamber and then tip the rifle until the muzzle points down, allowing the bullet to fall by its own weight into the rifling. Then lock off the gauge, tip the rifle back and remove the gauge as normal.
Try these methods and see if it helps. Ultimately, whatever you do, you will not get the same reading every time so you will have to take the average or just eliminate the ones which look wrong.