A two-hour layover will almost guarantee your bags will beat you to Maui. 30 minutes to transfer a bag is reasonable as a minimum. HA is actually very efficient in their baggage handling so I'm not sure why you seem to have such tough luck because it is the exception. My point is there's potential to minimize your time at airports if you get to OGG as soon as you can, because there's a pretty good chance your luggage may beat you there if you don't. If it doesn't, you're just waiting at OGG instead of HNL. What the staff says is fine, and they are indeed telling you what a "safe" connection for your bag is, but in reality, there's a good chance that you could be on your way from OGG if the luggage transfer is faster than they are telling you to prepare for, which it almost always is.

Also, a lot of passengers sit at the carousel for their bags and get then get annoyed (after a 10 or 15 minute wait) when their bags aren't with the bags from the plane they came in on, head over to complain at the baggage counter, only to be told to go and look at the collection of bags from previous flights at the makai side of the claim area that have been sitting there for a half-hour or more. They probably laid over in HNL for 2 hrs and then watched the carousel for 10 minutes before it started spinning, and then another 10 until the last bag came out. I'm probably already home by the time they're climbing aboard a car rental shuttle.