So #1 - I don't want you to risk a Chase shutdown. I will recommend some Chase cards here...but you need to determine if you're at risk.
1) You and your Player 2 could both open a Marriott Business card. This card is NOT subject to 5/24. You earn 75,000 Points for spending $3,000. You stated that you will soon have 40,000 SPG points (which becomes 120,000 Marriott points). With these cards, you would earn 78,000 Marriott points each. I'm not going to bore you with the details of how to combine those points but you could get them all into one Marriott account through some different methods and you'd have 276,000 Marriott points total. With this total you could redeem though Marriott nights & Flights for
120,000 SW RR points and you'd get a bonus 7 night cert for a cat. 1-5 property. 120,000 SW points will likely cover $1,700 - $1,800 in flights.
2) You and your Player 2 could both open a Hyatt card. This card is also NOT subject to 5/24 and the signup plus MSR would earn 42k pts. Hyatt points transfer to Southwest at 5:2.4 I believe and if you transfer 50k points you get a kicker. In theory you could transfer 8k URs (if you have them) to Hyatt to hit that 50k mark and so that signup + some URs could be worth 29k-30k Southwest points (times 2 = about 60k Southwest points worth $850ish). (I know these are rough numbers but I'm not as familiar with the Hyatt program)
3) You could earn AMEX MRs from cards like the BGR, Biz Plat, BlueBiz+, and Biz Green, and transfer to SPG then to Marriott. AMEX MRs are 3:1 to SPG and then 1:3 to Marriott so it's basically 1:1 from AMEX MRs to Marriott. Then you could revert to step 1 and make them Southwest through a Nights and Flights.
I believe those are all the ideas I can come up with

Again I'll reiterate that getting Chase cards when you are > 5/24 (even though the cards themselves are not subject to 5/24) can be risky due to all the shutdown reports.
EDIT: I should also add that you could just take your 120,000 Marriott points (from your 40k SPG) and based on the new conversion program that I think it coming soon you can turn that into 50,000 SW points (without the whole nights and flights thing).