This is very useful information. Thank you very much, all.
I suppose listening to the advice of an actual baggage handler is well worth it here.
Annoying, but I'll pick up the bags and haul them back and forth to the Renaissance.
FWIW... On the phone an agent researched it and said the rule is 6 hours... Though I have definitely had checked bags through longer connections than that. I suppose there is a certain amount of discretion an agent at check-in can exercise.
RL... I think it is a broken fare. I had to re-ticket my original itin and was offered the overnight for the same price as a tighter same-day connection, so took the overnight. When looking on dl.com it shows as a "multi-city" itin (as opposed to NYC-HNL) so I assume the fare has been broken up. This required a whole lot of work with the re-issue desk so not sure why cost was the same as single through-fare.
Thank you also for the DL to HA (but not inverse) interlining comments. Luckily, we do only need this on the outbound so that should work.