First, does 2.400 inches sound like a relatively small max OAL for a .308WIN 165gr Nosler BT in a Rem. 700 sps?

That is what I got for my max OAL in that bullet weight. I tried loading the bullet .020 shorter, and when I chambered the round, the tip of my bullet was bent over. It chambers fine when I seat it at 2.290 which was just the next step down I tried, but I'm afraid to seat it any less deep for my bullet tips' sake. My brass is used, but FL sized and trimmed to 2.050. I'm using Redding dies too. This is the first time I've tried using my OAL gauge, and I'm inexperienced with it. I've always just seated bullets according to what the reccomendation in my manual was for that load. Anyone know what might be going on?

The case length of 2.050" is too long. The maximum length for the 308 Win is 2.015" and trim it to 2.010".

A length of 2.40" is way too short for a 308 and in particular with that long 165 gr BT. Don't know how your measuring them but lay a ruler along side and make them 2 3/4" long. Then try them in the magazine with the firing pin removed from the bolt.

What are you using to measure with?

Your cases are way tooo long, i used to load 308 and all of my case were trimmed to 2.00" thats what the manual i used said anyway, but i always seated my bullets according to my rifles chamber depth, all rifles will be different, but somewhere around 2.800 should be a starting point i remember on a 150gr Gameking I seated them at 2.825 but 2.400 is way too short. On the other hand are you measuring to the ogive or OAL. You should have never bent the tip of the bullet, but your sayin you bend the bullet tip by seating it deeeper, doesn't make since to me, i don't know what kind of OAL gauge you have, but sounds to me like you need to find the nearest trash can and get rid of it and buy you a good digital caliper for measuring OAL.

Maybe by seating the bullet that deep you are compressing the powder to the point the bullet tip is bending