Update!
Here's my strategy thus far: For S/M/L sizing, I've gone from L in high school to M in college to S post college. My weight has not changed, I've just realized what size I actually am.
Small is usually 14.5" in the neck, which is very close as you can see in the photo, but it's usually 33" in the sleeves, which is okay if I keep tugging on them. This shirt is 34", which is perfect. I don't have to be conscious of the sleeves since they rest perfectly at my wrists. The body of a small tends to be perfect too, just a little short which makes tucking in a frequent task. Ideally, Small Tall would fit the bill, and I'll try the Express Small Tall white and black 1MX shirts at some point.
All that to say, Small shirts work well if I want it to fit in all but the sleeves, so if it's casual, and I'm going to roll up the sleeves and go untucked, it's perfect. Truly couldn't be better. If I want to wear it under a blazer or suit, though, I won't be showing much cuff, which is a problem.
Enter the BB 14.5/34 which I mentioned in the above post 2 weeks ago. I finally pulled the trigger and ordered it, posting a review here. The neck has way more than two fingers of space, but it looks decent. Everything else is killer, killer, killer.

I'm getting the button moved over a touch by the tailor for $5, so we'll see if that gets me a step closer. Anyone else have a button moved? I know, I should be able to move a button by myself, but for $5...at least it'll be done right.