danny hay i wanted to let you know 5 gal pots are pretty big you really dont need to go bigger with roots you will have a main ball and then it sends off some longer ones looking for water just because you see a few coming out of the drain holes is normal since that is were the water flows out and is the last place that is wet you will also see some doing thiis on the top of your dirt also i had the same issue and when my plant was done the root system was like i described a main ball about midway dwn my dirt and had others "feeders" streching everwhere looking for water/oxygen it is your plant and your choice to transplant it but baware you can cause shock that can be pretty hard on your plant for a little bit. Ill bet that if you put it in a 10 gallon pot in a few you will see roots growin out the drain holes again good luck buddy
I found some pics of what I would call being root bound, or almost root bound. See how the roots have no where to grow?
Mine aren't going to look like that though. See how the off shoots kind of look like a fish bone with smaller off shoots coming off them? With the root growth stimulator I'm using thost little off shoots that look like the fish's ribs are going to be a lot longer, and they'll have their own off shoots. So when my girls get root bound, they are really going to be root bound.
Here are some more examples of others that used the same typs of growth accelerator. Some are side by side comparisons with roots and some just showing growth. And you take a look at that Pumpkin and tell me roots don't mean that much with growth size.
I already know for a fact that the root span has a relation to the folliage span. But I also remember learning in school that tree roots are twice as deep as the tree is tall, so I'm pretty sure the roots also have a relation to height. Plus the bigger root systems can absorb more water, nutes, and everything else.
I've already thought about how I'm going to do the transplant as to not cause too much disturbance. I'm going to get a drill bit with a cutter/grinder on the end. Kind of like a router tip. I'm going to lay it on it's side and cut away the bottom. Then I'm gonna lay a towel down near the bottom and stand it up on the towel. Then I'm going to start vertical cuts on 2 side opposite one another and cut half way down. I'll then put duct tape over the cuts so it doesn't split when I complete the vertical cuts. Then I'll finish the cuts and put more tape on the bottom. I'll prepare the new pots with a layer of soil on the bottom at the right thickness to put the top of the soil in the old pot at the top of the new pot, and using the towel to keep anything from falling out of the bottom I'll put the old pot into the new pot. I'll remove the towel and start putting dirt around the sides of the old pot. When the soil reaches the 2 lower pieces of tape I'll remove them, continue adding soild around the sides, and do the same thing with the 2 higher pieces of tape when I reach them. Then I'll finish adding soild around the sides to the top of the planter and carefully remove the 2 sides of the old planter. I'm hoping that keeps the root disturbance to a minimum. And I'll also use more of the growth accelerator in the new soil and and all along the meeting of the 2 soils, it also helps with transplant shock.
Seriously though, and I don't mean this in a negative way. If you're not using anything to accelerate your root growth, then you're dealing with a different kind of root system. When you change the roots characteristics, the rules change with them.
Oh, and the way I've been watering, I haven't had much run off if any. I've been experimenting a little so I can learn to water without over watering. I started with 1 cup at a time and they're now up to 6 cups at a time, but I learned a lot with the flushings I've been doing and will be watering with more water from now on. But the run off isn't the reason that they're at the drainage holes.
Thanks for the concern though, I really do appreciate it.
I know this is going to sound like a real newbie type question, especially after this post (I'm an advanced newbie, but still a newbie. lol). What's the best condition of ths soil so it stays together better while transplanting (dry, moist, saturated, etc...)
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All i can do is stress science in the face of an overwhelming forum paradigm. Nice repeatable, provable science. Feelings and beliefs are not a factor. 
