My editor got picked up by a national subscription paper, and when I approached them, they said yes, they'd carry me, too, based on his recommendation. So, for a couple of years, I rubbed column inches with the best of the liberal media, imo, such as Molly Ivins, Hillary Clinton, etc. You can see who they still carry at www.liberalopinion.com. The only reason they dropped me is I quit producing when my mom died. I just didn't have it in me, then.
Earlier, I'd approached a few syndicates, but was turned down, mostly because of not enough years of material being published consistently, plus they want YOU to tell them HOW to market you and who your market is, the same as book publishers do these days.
I'd not expect to make anything but pocket change from columns, unless something hits just right and you get picked up by the big guys. The one thing it can lead to is enough to fill a book and maybe get published that way.
The proliferation of so much writing for free on the internet has really made it more difficult to stand out, too, imo. I do have some pieces which have been published on the internet, but I've never pursued anything significant that way.
The best advice I ever received was to start local and go on from there. Good luck and most of all enjoy it!