I’m taking a look at Hawaiian’s MCO-HNL schedule. Flights begin on 3/11/21, bi-weekly departing Tuesdays and Saturdays. Hawaiian opens up its calendar 331 days in advance, so you can search and book as far as early February 2022 right now. As we approach the busier summer travel months, the schedule shows flights on the other days of the week but those appear to be on their codeshare partner JetBlue from MCO-SFO with a layover, then SFO-HNL on Hawaiian.
My wife has a Hawaiian credit card. Main Cabin (Economy) award fares on both Tuesdays and Saturdays are consistently 26,250 miles + $6 taxes; First Class awards are 130,000 miles + $6 taxes. I did not see any 40,000 miles saver awards available in First Class. Keep in mind HA’s awards are on a dynamic range based on inventory and demand. I saw some Economy awards costing 35,000, 43,750, 52,500, and 70,000 miles in November and December, and as much as 87,500 miles in January (although it’s likely awards are not fully loaded in yet towards the end of their schedule). Per Hawaiian’s award chart, there is no “discounted award amount” for First Class awards; it’s either the 40,000 saver or 130,000 standard. Again, I’ve never just happened across a First Class saver award, and I didn’t see any when I just scanned all the way to the end of schedule.
I’m really concerned you’re already at 4/24 and appear ready to hit 5/24 without considering any Chase cards. Chase UR doesn’t transfer to Hawaiian, but they’re flexible as “cash” if it makes more sense to book the cash fare through the Chase travel portal. A First Class ticket averages about $2,000-$2,500. If you had a Chase Sapphire Reserve that gave you a 50% bonus on redemption, where 1 UR point = 1.5 cents (per point), that’s 133,333-166,667 UR points – not really the best value, but it’s an option. An Extra Comfort ticket that
@CaptainAmerica mentioned ranges from $500-$1,000; or 33,333-66,667 UR points. If you can pick a good seat up front, that’s a pretty good value. I’d just hate for you to foreclose yourself to Chase cards (especially their business cards), where you could rack up a sizable amount of UR points.
You might want to wait on opening the Hawaiian credit card until you’ve built up enough Amex MR that you’d want to transfer to HawaiianMiles, combine and you’re almost ready to book. The personal Hawaiian card’s $2,000 MSR (and the Hawaiian biz card’s $1,000 MSR) is low enough that they should be fairly easy to meet in a short amount of time to earn those points and have ready to book within a month or two of opening the card(s).
Another concern is you’re trying to plan a trip less than a year out. You’re starting from almost scratch, and we typically recommend giving yourself at least a year to get the points in place and another 11-12 months to start booking for the best deals. Hawaiian’s schedule is already open through early February. Those 26,250 miles Economy awards are the lowest available, and may go up the longer you wait to book. I know you’re looking at First Class, and those won’t get more expensive than 130,000 miles but there is limited availability. I see some dates where there are no First Class awards available and many others with 2-5 First Class awards available.
Amex's business charge cards (especially the Business Platinum and Business Gold) and the Blue Business Plus (BBP) seem obvious candidates that won't have any 5/24 effects (since they don't report on personal credit reports so Chase doesn't see them and count them against your 5/24 status, and once you're an Amex customer Amex rarely conducts a hard pull on new card applications). They're all high SUB cards, with annual fees that can be justified or offset with credits and other benefits (no AF on the BBP). They also tend to have high minimum spending requirements, so without knowing more about how much taxes you pay, or whether you and DH are willing to put actual business expenses on credit cards, it's hard to gauge whether this is more than you can handle. Amex also has the Business Green and Plum charge cards that don't have great SUBs, but they have no annual fee in the first year and may be worth opening and holding for a year just for the "supportal" bonus.
Another thing about opening Amex cards is there are public welcome offers, targeted welcome offers, and what's available via "supportal" - that is, you should consider how much the supportal bonus is to the "supporter" and what the "supportee" will receive as a SUB. It takes a little bit of poking around to find the links and browser/incognito/vpn combination that'll get you the highest and best offer (or combined points in 2-player mode). Do a little bit of homework (or asking around) to educate yourself what the best offer is for a particular Amex card, since Amex SUBs are generally once per lifetime and Amex doesn't match better offers that might have been available or come out later.
An Amex cardmember CAN transfer MR into a spouse's frequent flier or hotel loyalty accounts if the transferee spouse is an authorized user or hold an "employee" card on the transferor spouse's Amex card. So DH could accumulate MRs, then transfer those MRs to your HawaiianMiles account if you are an AU/employee on one of his Amex cards. You'd need to be an AU/employee on your spouse's Amex card for 90 days before he can transfer his MR to your frequent flier or hotel loyalty accounts. As I mentioned previously, it's not a good idea to get added as an AU on your spouse's
personal Amex card, but you could be added as an employee on your spouse's
business Amex card without the 5/24 implications (since the primary cardholder's Amex business card doesn't report to personal credit reports, neither does the "employee" card to your personal credit reports).
The other way to do this without being added as an AU/employee on your spouse's Amex card is as you mentioned, DH could transfer MR to his HA account, then transfer the HawaiianMiles from his HA account to yours without fee if/when you're holding a HawaiianMiles credit card.
Keep in mind under either scenario, you'll pay Amex's excise fee for transfers of MR to domestic airlines of 0.06 cents per point (capped at $99 for any single transfer), i.e., whether DH transfers his MR to your HA account or DH transfers his MR to his HA account, in addition to the fee on transferring your MR to your HA account.