Greysmith is on the right track. Think of most roots on a fig tree as going straight away from the plant until they hit something, then growing along that surface. If you go from a cup to a very large pot, then you run the risk of the pot having very few roots anywhere except right in the middle and then running rings around the outside. This is not a good situation. Probably, if you did it this way and every few months, somehow sliced any roots that were encircling the pot, eventually you'd get a nice root ball. Or you used the fabric pots (just have to water them like crazy) it probably is ok too, since in the fabric pots they do less circling once they hit the fabric.
At the end of the day, pot culture tends to lead to roots circling around the pot, which is not an efficient use of the plant's resources, and it doesn't optimally supply the top with water and nutrients. So you have to take measures to reduce this problem. There are many ways to do it. Gradual up-potting reduces the short term effects, but the problem is still going to be there.
No matter what, when I up-pot I always take a utility knife and slice along the sides and bottom a couple times to remove or reduce any circling roots. You don't necessarily have to re-pot (shake or rinse the soil off the whole root mass, then cut it down to size) as long as you sever most of the longer roots. I have done this at all times of the year with success. Never seen a plant stressed afterwards. I believe that re-potting is stressful mainly because of all the smaller roots that are severed, rather than the long ones. So I try to sever the long ones while leaving most of the smaller, shorter ones intact. Five or Six good slices should do the trick.
If a pot is the tree's permanent home, a full re-pot is still a good idea every few years for long term vitality and vigor. But it's a ton of work, and I have too many trees.