The Tavern

Under what circumstances do you (totally and voluntarily) skip a timed portal? I basically never do; but I lose a lot of promising characters in Ice, so maybe I should start skipping it when I lack rC?

I never really skip, but sometimes I back out.

I recently had a character come within a hairs breadth of dying because he was completely ill-equipped to deal with the cave's simulacra. Luckily he survived because the simulacra can't follow you out the exit.

Personally I get killed most in fire caves.

I never skip them voluntarily. I feel frustrated if I don't find one before it expires.

Ice Cave is the most deadly for me, too. Go slow and use the tools you have available.

Well yes of course. The immediate motivation for this post was losing a one-on-one fight with a freezing wraith, for which I'd berserked. I was probably going to leave after the first little pile of loot; but didn't get that far.

Yeah simulacra are scarier than they look (and than the game suggests they are) IMO.

I learned the hard way not to enter an Ice Cave without rC+. But since the introduction of the gauntlet (or the demise of the Labyrinth), I lost a lot of characters there.
And I'm a lot less inclined to enter a portal when I'm trying a streak. Otherwise, I embrace the risk most of the time.

The problem with skipping Gauntlet is that I don't really have a sense for which characters shouldn't skip it; and it's rewarding (and fun!) enough that I wouldn't want to skip it every time.

Well, I mean with gauntlets at least you can pre-scout all the monsters and rewards and decide if you've got the chops and the rewards are tempting enough and bail out if not.
Most timed portals have a bail-out option, so it's often worth entering them even if they are in the 'iffy' range for you, but completing them is a different story than just entering the portal.

True, though when I lose a character to Gauntlet it's almost always to the minotaur, not to the actual gauntlet. And one can't pre-scout e.g. what weapon it got.

1) If I get badly shafted, for example from D:9 to D:12 and again to D:15 before doing Lair, I probably won't enter timed portals which I possibly find on the way back up.
2) I mostly skip the Desolation (had a couple of bad experiences there), unless I find it really late and feel really confident.
Otherwise, I go for all of them. Peeking in is usually safe anyway.