I would change them all into support area conditions, that can be turned into minions at river and swamp sites.
That one could be interesting. Perhaps the watcher could also have a trigger to change the site type as well. Something like:
Response: If an unbound hobbit exerts or uses a special ability play the next site. That site is a marsh until the end of the turn.
Skirmish: If more than one tentacle is assigned to the ringbearer you may discard them and remove (4) twilight to make this condition an eleven strength minion with four vitality until the regroup phase and have it replace those tentacles in that skirmish. It is strength plus two and damage plus one for each tentacle discarded in this way. This is still a condition.
The tentacles could be something like this:
Shadow: If the fellowship's current site is a marsh or a river and you cannot spot a minion without the tentacle keyword you may remove (2) twilight to make this condition a four strength minion with two vitality until the regroup phase. This is still a condition.
Each time this minion wins a skirmish you may play a tentacle from your discard pile.
What do you think?