You can't always call it perfectly, and there's still a lot of uncertainty with covid. Normally I would say that if you're airline-bound, be wary of locking yourself into a contract which might hold you back from career progression but under the circumstances it's too hard to predict.
Good bet most of the regionals won't be paying for ATP's for a while, although even that's not certain.
How long to upgrade? If that's where the obligation starts, might as well sit tight and see how things look at that point. I expect we'll have a better idea by mid/late summer as vaccination closes in on herd immunity as to what the (domestic) airline recovery is going to look like.