Different immigration offices have different policies, and this question may be immigration office specific.
You can find my FAQ about the 60 Day Extension of Stay Based on Unable to travel due to COVID-19 at
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That provides best practices.
>Am I allowed to FIRST get a 30-day extension (which would be valid until around Feb 5th), and in the meantime apply for the Covid Extension (which I understand is on until Jan 25th)?
At most immigration offices, you can apply for an extension of stay when you have 45 days remaining on your current stamp. For the 60 day extension of stay based on unable to travel due to COVID-19, the extension of stay begins on the date you apply for it (at most immigration offices). You can only stay 60 days past Jan 25, which should let you stay until Saturday, March 26 (Thanks
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for correcting my math!).