Fingers crossed on the CIP #2. There’s a good chance you’ll be approved even with the new Venture card. Congrats on the Venture approval!
Ok, I don’t do bank funding, so I can’t comment.
Yes, you can use CIP #2 to buy MCGCs at a grocery store and use them on Plastiq to pay your mortgage, but it may not be a very cheap option to hit MSR. Assuming you buy a $500 MGCG with a $5.95 activation fee, that’s a 1.19% fee. Plastiq tacks on another 2.5% fee. If you can earn gas reward points at your grocery store on the MCGCs, and you have FFDs on Plastiq, that’ll lower your cost.
@speedyfishy may have more experience with MCGCs from giftcards .com, which does have a $6.95 activation fee on $500 (1.39%), but I think earns 3x UR on the CIP to help offset that fee.
As for Venmo, I haven’t read anything about Chase having any issue with using Venmo to meet MSR. You could, as you mentioned, make a P2P transfer to your son using Venmo and hit MSR that way. The concern is on the Venmo side possibly shutting down your account and holding funds in limbo if they suspect something fraudulent or illegal. It’s best if you have a seasoned account, and make the transfer(s) look as natural as possible, e.g., payment for tuition, rent, new clothes or a computer, use emojis, etc. Have your son withdraw the money into his bank account then write you a check or something. Don’t Venmo funds to DS, and have him Venmo the money directly back to you. Also note that Venmo has certain transfer and withdrawal limits for new/unverified accounts, and limits on how many new cards you can add to your Venmo account in a rolling 6 month period. Check those. Venmo does charge a 3% fee for payments using credit cards, but you earn 3x UR on the payment and fee on the CIP. I did read some people are having issues adding the CIP to Venmo recently. I hope this doesn’t affect you, but have a backup plan if Venmo doesn’t work.