If my hero is stuck in a web and Shadow Soul is halfway across the board, can I swap out of that web?

According to the rules, a web tolen only prevents you from spending movement points. So yes, you can swap places with the shadow soul... but the web token would stay with you, as it's not placed on the map, but on your character.

I know, it does not make much sense thematically, but Descent is not a simulation, it's a boardgame.

It makes as much sense as if you swaped with the Shadow Soul and you keep wearing your clothes.

sithbunny36 said:

It makes as much sense as if you swaped with the Shadow Soul and you keep wearing your clothes.

True enough.