You can definitely pot up. Even before this point by more than a day or 2, most likely... The next size should be appropriate, though. If you are going to 3-5 gal, you may want an intermediate size for 2-3 weeks, then pot up again. No worries of a few days off. There is an 'optimal' path but even if you lose a day or 2 that's not much relative to 100 days. If you overlap grows, it'll be difficult to time everything perfectly in a consistent way... so, shit happens and it still turns out perfectly fine.
if you pot up to a larger size and the plant can't drink fast enough, the water absorbed into the medium just sits there and stagnates growing weird shit -- same reason you don't want to leave water out for long periods of time sitting around.
How fast it drinks is how i determine when to pot up too. It's the most correlative trigger. Once you approach 1 days between irrigatons, you know it's drinking the water fairly quickly and can hit the ground running in the next size up. This assumes common sense wet-dry watering cycle. If you like to water early, maybe as it is well into daily irrigations with limited dryback.
Roots out the drainhole - not a good trigger. I have some recently rooted clones with roots poping out the bottom, but it was not well-rooted, yet.
Size of canopy relative to volume of medium is another good trigger... That's what is driving the drinking rate anyway - potential transpiration.