Ok - I've remained silent here so far (work was so busy this week), but I'd like to weigh in with some advice. I really think you should re-evaluate your position on business cards in general and consider the Barclays Jetblue Business card. Any side hustle can potentially qualify you for a biz card. Things like mowing lawns, babysitting, consulting work, selling on e-bay, teaching piano, tutoring, and so on could all be considered a small business sole prop for this purpose.
https://cards.barclaycardus.com/banking/cards/jetblue-business-card/
This offer is pretty good:
Earn up to 60,000 bonus points // Earn 50,000 points after spending $1,000 in the first 90 days and earn 10,000 points when a purchase is made on an employee card in the first 90 days.
And to my knowledge, JetBlue remains one of if not the only airline mile/pts currency where you can do family pooling- so you could combine your points.
This card also earns 2x JetBlue points on restaurants and office supply stores. You might be able to funnel some of your MSR through gift cards sold at Staples or Office Max to pad the earnings a bit! Although with just a $1,000 MSR you'll probably knock that out in no time.
I reached out to my man
@PolyRob for a little JetBlue card intel as this isn't a points currency I've been spending time with recently. With a low $99 annual fee and a $1,000 MSR, this offer is fantastic. It gets you free checked bags, awards you 5,000 pts on your card anniv. I don't have a great handle on what Jetblue points are worth, but a quick google search shows that you're probably in the neighborhood of 1.4 cpp which makes this a better deal than a CSP which had previously been recommended.
To be honest, if you know what airline you're going to fly, and it's a domestic trip with one of the major carriers, I say it's usually better to earn that specific airline's currency than more flexible points. Earn JB pts to fly JB... save URs for other travel expenses.
If you each applied for this biz card and managed to get approved, you'd probably be looking at $1,500+ in free flights with free checked bags. AND since they are biz cards, you wouldn't affect your 5/24 status leaving Chase cards as an option in the future. There is no support link for the Jetblue cards, BUT if you opt to go in a different direction (i.e. Chase) there are support links out there for that.
With that in mind, you also might consider joining our DISchurners reddit group which has some great info, guides, and ways to pay it forward to the group when you apply for certain cards (i.e. support links). If you're interested, drop me a quick PM here on the DIS.
Thanks - hopefully this helps some!
EDIT: Ok...am I crazy or am now considering an application for this card even though I have no intentions to fly JetBlue and I have like 800k SW points???
I wonder how else I could use these points! Off to research... haha!