Since you are on separate tickets you will have to reclaim your bags and then walk to the inter-island terminal to recheck (probably about a 7-8 minute walk). AA used to interline bags onto separately booked Hawaiian tickets but they quit that years ago. It is still worth asking the AA agent at check-in but everytime I’ve asked over the last 3 or so years it has always been a hard no and that’s as an executive platinum traveling with 1 bag in first class on AA and connecting to first class on Hawaiian LOL.

I do a DFW-HNL-KOA connection from AA to Hawaiian 4-5 times a year when the nonstop DFW-KOA isn’t running. I almost always book separate tickets due to the insane price difference one can encounter when bundling them together on one ticket. When I book, I aim for a 3 hour layover but your 2 hours should be fine as long as you are on time. I would suggest checking in for your Hawaiian/Ohana flight 24 hours out and printing out your boarding passes for that flight. Also, hopefully you have TSA precheck and can enter that into your Hawaiian reservation because the inter-island security line can sometimes get brutal in the afternoons. In terms of your return flight, a 1 hour connection on separate tickets with checked bags would be pretty much impossible.

Also, unless you’re visiting family or friends, I assume you’re going to the Four Seasons Lanai? You may already be aware but there is a Four Seasons Lanai lounge at HNL airport. I don’t know if you’ll have time to enjoy it but it’s nice and they can even check you into your room there. Have a fun trip and hopefully everything works out ok for you.

Quick update: So I told my wife all your kind replies and - despite being normally the one holding the bucks together- she has suggested to choose the ‚private‘ Lanai charter saving us a few hours; given the difference of $600.

Good wife