| Peruhain of Brithondy |
DM's call, but I'd say that "entangled" is a condition you can only apply once. You're either entangled, with all the appropriate penalties, or you're not. The only advantage to entangling your enemy multiple times is that they have to break each entanglement (net, scrape off the sticky goo, break out of the web or entangling foliage, etc.) to end the condition of being "entangled."