Negotiating a contract? Get insurance requirements EARLY!
It happens a lot: a business is close to landing a lucrative contract and in the final stage, they send their agent the insurance requirements (so far ignored) only to find the extra coverage required will cost a bunch of money.
True Story: a local IT firm was close to signing a large contract with a worldwide computer company, then discovered at the last minute that the insurance requirements easily topped $50,000 annually. Would’ve been much better to find that out sooner.
I know a painter that bid a job, signed the (unread) contract, finished his work, and submitted his invoice. The general contractor said, “Great, just get us a ‘Certificate of Insurance’ and we’ll cut you a check.” The painter asked his agent for the certificate but was told he doesn’t have all the requirements and to fulfill them would cost $2500. The same amount he was supposed to get paid! Ouch.
If the insurance requirements are looked into early on, sometimes the extra cost can be worked into the negotiations, or the requirements reduced or even removed.
Contractors and IT companies, yes, but also wholesalers, government contractors, and any other business that has the chance to land a big contract is likely to run into this at some point.
So ask for a template copy of their vendor insurance requirements early, and nip this in the bud.
Tom Allen, Commercial Insurance Agent, CIC 
This is very good advice. Unfortunately I don’t live in Hawaii but if I did, I’d make you my agent. My guy over here has had many chances to tell me this as we’ve run into this twice now, but he never has.
I was just reminded this week that this also applies to lease agreements. Make sure you know what the insurance requirements are before you sign that long term lease.