Is the cherry eye really bothering him? How severe is it?

From what I've gathered, its usually more of a cosmetic issue than a health issue...but some of them can be bad. I suggest you seek a second opinion, if you're not comfortable with your vet jumping to removing the gland. It may not be necessary.

Also, has your pup been fixed? ...If not, I'd wait and see if they could do both at one time.