I've yet to see an "Association" deal worth a damn, for commercial insurance. Narrow coverage, and an MGA who swears that they'll create the industry's "own" program once they have a reserve built up...
But, people are stupid and greedy. 80% of association program's sales come from people just checking a box. Sure, insurance is a pain in the ass, but for a few thousand bucks, it's worth shopping yes? A guy in a suit who represents "you" is no better than a politician, and should be treated as such.
If Rucking Insurance Services doesn't find you the best cover for the best premium, we'll tell you. RIS does better long term by ignoring the short term sale. Some of best sources of referrals are from Business Owners who I told to go with a DIFFERENT proposal than mine. It happens, and it happens to be the right thing to do.
Now, this is typically for General Liability. You can get some discounts from loose organization's for business auto, and I know of NO discount programs for Workers Comp.
Remember, if it's cheap, it's because it's cheap.