you could hold a line pretty quick out of LAX on the 737, and within day 18 months -2 years be doing regular trips on the 737 to Hawaii.
you could also aggressive pickup any Hawaii trips (assuming, but not likely, that they’re available) if you’re sitting on reserve.

I think they would be your best bet, or maybe SFO doing the same thing.

it’s definitely doable.

Depends on where one wants to live.... Live in Hawaii and commute to West Coast.. Lots of jumpseats on a NB for 5+ hrs....

I wouldn't base my decision on bidding 737 and getting Hawaii trips... Flying and a/c change way too often to base a career on one a/c doing a certain type of flying long term. Also what's to say the OP will be able to hold all Hawaii trips within 18-24 months? What one gets today does not necessarily mean it will be there tomorrow. What about if the OP wants to upgrade or something else that means he cannot stay in LAX/737... Too many variables to simply say "bid 737 LAX and life will be good for the next 15-20 yrs."

UAL is probably superior in many work rules and pay, it really comes down to the OP's QOL goals and how long he/she is planning on staying in Hawaii... How much of that extra UAL pay or work rules will be eaten up by commuting/crashpads, stress vs. driving to work?

If I was intending on living on the mainland, I would def. be wanting to be at a mainland carrier. Cannot fault anyone currently commuting at HA , applying to other airlines

Interisland flying is hard to beat for qol.
There is a financial hit, but I do like to drive to work and come home the same day.
No bags, TSA, hotel vans, or time zones.
Having property and another income means you have beat the two biggest hurdles.

HAL=Boutique Airline 👍

While normally I would agree with you, we’re not talking the Boise to Denver route here. Hawaii flying will be around for the 6-8 years that he wants to be in Oahu, and that flying will be done from LAX and SFO. Both bases are junior-that hasn’t and won’t change

A big issue on the island is schools for the kiddos. Either sub par public or rather expensive private.
with a house there I’m guessing you know this already. As was mentioned 717 QOL can’t be beat. But I fear the growth at HA is slowing down. UA retirements are appealing and a real Major. Though decision, good luck.

It's pretty simple. If you want to live Hawaii then it's Hal. If you want mainland then it's Ual.

Myriad of considerations. For many, the flying they do here is unachievable right off the bat (within a few yrs) at United. Also, our trips don’t have you gone from home much, another plus.

On the the negative side: lack of retirements, complete focus on one hub, cost of living.

Not so so black and white.

Thanks everyone for the responses!

I'll have 22 years left of flying. We want to give living in Hawaii a shot for our next 5-8 years minimum while the kids are young. We may stay longer, but after living like gypsies in uniform (moving a lot) - its just really hard for us to say we can be at a place "forever." It makes sense to start w/ HAL, even later if we move back to the mainland at least I'm visiting fam at HNL to start my trips, hope to be on 330 or 78s by then to string more days on/off to lessen the number of times I commute 10-12 hours for work.

Agree! Can you please expand on the "flying they do here"? HAL or UAL? Do you mean a chance to get a 330 at the start of class w/ HAL?

Also, please explain "lack of retirements"? I understand both have 401k contributions (HAL is 15% and UAL is 16%) but what else? Is there no profit sharing annual checks at HAL or UAL?