I like a messy den.
I've seen some huge beauties that grew out of their pot long ago and have keikei's we'd be growing in 12inch pots. The only issue is making sure the plant gets the water it needs. the ones i saw were growing in a tropical greenhouse on wet matting.
For the rest of us though, a re pot is alot easier. I would choose a pot you can get most of the roots in with abit of space for root growth. its ok to have some root hanging over. Getting fresh medium is usually the most important aspect, as it gives it what the plant wants most.
a repot would make it easier to keep it watered well also
wait for a few other replies though, I dont want to be your only advice