I think DUD-CHC and WLG-NPE are ATR? CHC-NSN, NSN-WLG either S340 or Q300. TUO-AKL and AKL-KKE either 1900D or J32.

The ATR does have overhead bin slightly smaller than 737. My small rollaboard fits these (just).

The S340 and Q300 have tiny overhead bins, only small enough for purse, small backpack. Underseat storage is also small. If flight is lightly loaded they may let you take larger item onboard and strap it into an empty seat.

1900D and J32 has no overhead bin and only tiny space underseat (one row not even that). Again if load is light you can put small bag on an empty seat, otherwise has to go in the back.

IIRC only the ATR (and possibly Q300 not sure) has a closet to put any bags that don't fit. So everything else goes in the hold. Since all a/c are boarded by stairs if your carryon is too big and not checked in already, you can get it added to the hold on boarding.

I've never had problem with 1 regular size + 1 small, but I imagine when flight is full with lots of luggage there may be an issue. 1 carry on between 3 is unlikely to pose a problem.