I'm starting to plan a trip to Kauai, HI for our family of 4 in 2025 (probably July, but maybe November during Thanksgiving break... I'm a teacher and have a kid still in high school). We planned this same trip in 2020 but had to cancel due to Covid, rebooked for 2021 and again had to cancel. So now I'm working on strategies for 2025. Here's what we have in cards already (we are both business owners, although mine is mostly a side hustle earning around $15,000 a year):

Husband: Business Unlimited (his business), Freedom Unlimited (joint with me), and a new Business Ink Cash (halfway completed the spend requirement already to get the bonus)
Me: Chase Business Unlimited (my own business name) , a new Chase Business Ink Cash (I'm just an employee under husband's Ink Cash), Chase Freedom (joint with husband), Saphhire (just me), Amazon, and United MilesagePlus

We are more than likely going to fly Southwest when we go to HI. I don't completely have my head wrapped around the benefits of a Southwest card other than the Sign-Up Bonus after spend requirement. I read something about 4 boarding upgrades per year, so maybe I need to call to have that explained. My goal is to use points to pay for our airfare. We currently only have about 70,000 but will have another 75,000 soon after Bus INk Cash spend requirement finished.

I'm trying to strategize which card(s) to apply for. Other than this Ink Cash husband got not long ago (that I'm on employee on), and my Amazon card (got a year ago), we haven't applied for any new cards in 2+ years (to rack up points for first attempt at HI trip). My credit score is 784 (as of 2 days ago). Husband's good also but don't know the exact score.

Side note: Neither our oldest daughter who still lives with us after graduating college a year ago and has a good paying job and only a loan for a pickup or our 18 year old daughter (will be a senior in high school) has their own credit card. I have them listed as employees on Bus Ink Cash so they help us get the spend requirement when they buy something. I might have oldest apply for a card so we "might" get her SUB? I don't have a clue what her credit score is but can have her request it.

I realize this is a long post... I'm grateful for any advice. It's not usually too hard to meet spend requirments, especially this time of year when husband's farming expenses are higher.