I once got stopped because they denied me a TN visa. That stoppage will stay with me they told me, so I have to report it everytime I go through and they ask me this question. But they say that's just an administrative denial, so it shouldn't stop me from going in for normal matters. However, a criminal record is more than just an administrative denial. If you need to go through to the US on a regular basis, then I'd suggest you do as they say and get that waiver and pay that exorbitant amount of money for it, because afterall you need to go to the USA regularly. What other choice do you have?
As for Hong Kong, don't you need a visa to visit HK? If you pass the visa approval process, then I'd say they are okay with you. But that mistake from 12 years ago is going to haunt you, everywhere you go from now on.