I have a bunch of cuttings in cups right now that are being acclimated to the sun. Most have 2-4 full sized leaves and a decent amount of roots. The roots do not look crowded in the cup but I was wondering when I should get them into 1 gal pots? I don't want to move too fast, but I am not sure how much more they can actually grow in the cups. I was thinking getting them into a bigger pot with a mix that has some nutrients in it may speed up the growth.

I've had mine in the cups for 2-3 months now with no problems.

Patience is a virtue. Better to wait a little longer than to be in a hurry.

I am not really in a hurry. I'll leave them be if that is what's best but I am just wondering what the optimum time is for transplanting? How far do you let them go before moving them up?

I let the roots in the cup and the leaves up top tell me when to transplant.  I like to see a decent bit of root binding, myself.

I'll let them go for a little while longer I guess.

If there were massive amounts of roots, and you're going to need to put into a cup/mix anyway, I would just up-pot it now, there is always risk when repotting anything, so the less transfers, the better.

well that one just went straight into the ground. Just kind of an experiment since I have extras so it's no big deal if it does not work out.  

Being in FL, as long as that thing stays well-watered, I seriously don't think you're going to have a problem.  But if it hasn't been in sunlight, I would allot it some temporary shade or filtering (umbrella, landscape screen, etc.)