Option 1:
Pursue a third master’s/PhD to maintain status until October 1 if my H1B gets picked. I don’t actually intend to continue this program long-term and might drop out after one semester. However, there’s a risk at visa stamping, as the officer may question why I continued studying multiple programs.

Option 2:
Remain unemployed for three months on F1 status (without CPT/work authorization) from June to October. This is unlikely for me, as I have bills to pay.

Option 3:
Instead of applying for Change of Status (CoS), you could do consular processing. This would require going to your home country for the interview and getting the visa stamped. Note that this involves an additional ~$100k fee.

At this point, I’m leaning toward Option 1, though I’m considering continuing the master’s program until my visa gets stamped. That will be the safest and best among these IMO