Quote Originally Posted by stinkyattic
Sounds good to me!

As was previously stated... many problems are fixable with enough lubricant and a firm smack.

Seriously though, I actually let my plants get overly DRY before transplanting.
I think your medium has a bit to do with it too. You will figure it out for yourself once you get to the point where you are dealing with nearly-potbound plants.
I do find that letting the plant I'm transplanting dry out helps immensely in getting it to come out of the pot in one chunk. The soil shrinks up and binds together much better. Plus the roots help hold it together.

I haven't encountered a problem yet that couldn't be fixed with lube and a smack.