When we had Annie's surgery and considered Rosie's surgery, we were told by specialists that there are two glands in the eye that produce tears, the protruding gland in cherry eye being one of them. So, removal of that gland will cut tear production. It may or may not cause dry eye immediately, but there would be more of a chance of developing dry eye later in your dog's life. Rosie's tear production was on the low end when the doc measured it and that is why we elected not to have the surgery. Personally, I would not have the gland completely removed. There is a method wherein the gland is shaved or partially removed to make it smaller before it is tacked into the pocket. I believe the specialist that did Annie's surgery enlarged the pocket before she stitched the gland in. I'm certainly no expert--just putting out my two cent's worth.
If your insurance will pay for it in January, I would certainly wait. Cherry eye is only a cosmetic problem and there is absolutely no harm in waiting.
We also tried massaging the gland back in, but it always popped back out. I may have put this in my other post that I tagged you to read, but our vet was a specialist referred to us by our regular vet. She had a lot of experience, had trained under the top cherry eye surgeon and then made her own improvements to his method and had never had a recurrence happen in her practice. We were lucky to find here here in town. I would think NY would have a specialist and maybe your vet could refer you to one? [MENTION=14810]CCandMurray[/MENTION]
Also, keep in mind that the surgery can be done on both eyes, even if the other eye is not affected. Annie only had one cherry eye, but the vet did the surgery on both eyes to avoid another surgery should the gland in the other eye pop out, which was more than likely. This avoided Annie having to go under again and the expense of another surgery. It cost a little more, but not too much, and I'm so glad we did it that way.