1. You'll get more traction with carrying him off. Luring would require constant managing as he'll want to return to his post, but you can just yoink him.
2. Yes, you can enter it, but oh boy does it suck. It makes your heart hurt and your body feels wrong, like your blood is pumping the wrong way. It's a horrific experience, but if you stay strong you can get through it to the other side where folks are tentacle'd.