Good luck getting actual advice from these people - they'd rather whine about the state of the radio business than actually offer anything constructive.
In my personal experience, of the major syndicators, TRN is the most useless when it comes to following up with assistance after you pick up their shows. They'll try to clear as much of their programming as possible on your station - if you want Savage or Ingraham, be prepared for them to try to bundle them up with Doyle, Humphries, Tammy Bruce, or, god forbid, Roy Masters. It may be worth it, depending on the situation in the market, to clear another show of theirs to get Savage and/or Ingraham, but just know what you're getting into before hand. Once you've signed the contracts, you won't get much follow up from them.
Premiere has some quality people working for them, who will try to help with any problems. But, once you get past Rush, Beck, and Coast to Coast - they've got some weak products. They typically won't try to bundle shows together, but if those shows are already locked up in your market, you won't have much use for them.
Westwood's reps don't seem to know much about the technical side of things. but they try to help and are pretty good about following through. Again, though, they have a shallow pool of quality shows.
I haven't dealt much with SRN, so no comment there.
Jones/Cox has the best affiliate relations group that I've worked with.
For news providers, if you can't get ABC or FOX, you're in for problems. They are both quality products with great tech support departments, however.
Again, this is all stemming from my personal experience. Good luck.