Case A Question: By law, should I just feel no guilty of putting the $5,250 reimbursement into my checking account, or put it back to Roth IRA by certain IRS requirement?
Case A Answer: The 60 days is up, you cannot rollover the $5250 into your Roth IRA. However, if you haven't already made a Roth contribution, for 2020, you can do so at that time. Note: the technicality is you are not "putting the money back" (rolling it over), you are making a new contribution. Whether you put the $5250 into your checking account or Roth, the $5250 is still tax free*. There's no guilt involved.
Case B: Question: By law, should I just feel no guilty of putting the $5,250 reimbursement into my checking account, or put it back to Roth IRA by certain IRS requirement?
Case B Answer: The answer is the same as case A. By law, you have until 4-15-21 to make a 2020 Roth contribution.
*If your concern is that getting tax free assistance, and a penalty waiver, is double dipping (2 benefits for the same money), that is allowed in this circumstance.
Since the $5250 is tax free, you cannot claim an education credit on the same amount. That would be double dipping.
