@Cesar *********
The regular 30 day extension is just a formality as long as you have the paperwork sorted. It would be a shock to get denied that.
The covid extension is at the discretion of the immigration officer, and some offices have stopped issuing it altogether. The only way to know if you will get it is to apply, but you'll want to wait until as close at March 25th as you can (this is the last day under the current program) as it starts the day you apply if you get it and you'll lose any days you have left on your original extension.