CTListener (assuming you are in CT), if you ever make it over to Boston/Providence/anywhere in Eastern MA, check out Easy 99.1/Plymouth (I think they stream too). Their playlist has at least 2,500 songs. They have nightly specialty hours from 6-10 PM ("'60s at 6," etc.) that broadens the playlist even more. They play songs from the late '60s to today, although music from 2010-today probably is played once an hour, if that.How many people even KNOW 2,500 songs? Is there any semblance of a power rotation, or is the average listener likely to hear their favorite big hits just as often as they'll hear a song they don't remember at all?
I'm guessing your station is a mom-and-pop operation in a small town, not part of any rated market. I'm also guessing there are few or no major cities near it, and thus no big-market FM classic hits station for competition. More power to you if your advertisers and listeners support your little station, but I seriously doubt the average radio listener in your town is as enthusiastic about it as you imagine.
PS -- If you're still playing hundreds of '50s titles, be aware that many of those tunes' most enthusiastic fans now reside in your town's cemeteries.
This station is my favorite in the entire country.