Moe, do me a favor and go to your "Profile" and update your public profile, giving your location. It can be city/state (best) or simply your USDA zone. That way we all know how to answer questions. I know you are in "sunny" Florida, but conditions from Key West to the Georgia border are several zones different. Growing conditions are everything.
I root mine so differently than you, I can't even begin to answer your question. Mine are all rooted in 100% extra coarse perlite. That makes it easy to tug on mine when I think it is rooted. I also "gang-bundle" a dozen or more per bucket. Mine won't see a pot or potting soil until they have already rooted. That's just the way I do it and am sure many people do exactly the same as what you have done. They will be able to give you good answers to your questions.
I up-pot to 3-5 gal. pots when the roots have pretty well filled the 1 gal. pot. The only way I can tell is to invert the potted plant, holding on to the stem, hit the side of the pot in a few places to loosen the soil, and then allow the plant/root-ball to fall out of that pot. I then can easily see whether it needs re-potting or not. If it doesn't, I just slip the pot back over the root-ball, and it is good to go.