I did it for a pair of Kenneth Cole boots that were already 2 1/2 years old.
I think I spent $15 and it was well worth it for me. I got another 2 years out of them. I couldn't believe how well they fixed it, too. Perhaps I had no expectations.
I'm sure you being in NYC would be able to find a good place that does it.
The first time I lived in Spain, I had a host mom who was frequently taking shoes there. Obviously, there is a lot of cobblestone there that wears down the shoes, but the women I knew always made sure there shoes looked nice as possibly and made them last long as possible.
I haven't, but DH has had several pairs re-soled. I think it's worth it if the shoes are more expensive than the cost of the repair. I don't bother repairing mine because the shoes I wear most often for work at $50 where as DH's cost $200. Men shoes seem to cost more than women's.
If the shoes weren't cheap, you love them, and you can't easily find a replacement pair, it's definitely worth it IMO. One pair of cowboy boots I've had resoled 4x. I have a pair of Marc Jacobs pumps that need freshening up too.
I have had many shoes refurbished. If they are quality shoes/boots to begin with, they will last many visits to the cobbler. I used to have a pair of boots that were my aunt's in the 70's. Still looked great.
I think it's totally worth it, especially with a good pair of shoes. I take my boots and nice heels in to the cobbler almost once a year (depending on the wear), just to make sure they last.