If what you need is at the top of a mountain, no roleplaying it through will allow you to avoid needing to make whatever number of climbing rolls the GM decides (and that construct tells you there's a problem too, since that's probably not a decision that should need to be pulled out of thin air).
@W'rkncacnter's post above made me look again at your earlier post.
I don't really agree that just because there's a mountain to climb there should be "climbing rolls"...unless there are difficult decisions to be made along the way. An example might be:
"A bird is flying straight toward the cliff. Bob, you're a druid and you immediately realize it's strange that an owl is out and about during the day."
"It's a spy! Is there any cover we get to?"
"Well, there are a few small, stunted trees sticking out the rocks. You might be able to use those, but it will take a Stealth roll. There's also big crack you might be able to scramble to if you hurry. I'll need a Climbing check; anybody who fails will slide down partway, will have to save to avoid a little bit of damage, and will lose one round of climbing time."
But I would
never just say, "Ok, I'll need five successive climbing checks to get to the top of the mountain. For each failure (some consequence)." I just don't find that very fun or interesting.
Also, this is somewhat tangential to the thread topic, but something that occurred to me while thinking about all this that one reason that combat skill is separated from non-combat skills in so many RPGs is that so many games really are combat heavy, and if you to allocate the same points across combat and non-combat, most people are going to go heavy in the combat. So one resources goes into improving combat, and another resource is spent on skills.
It's really the same problem as with spell choices: first you load up on combat (offense, defense, support) spells, and then
maybe you take some utility spells, that you may or may not end up using. (Ritual casting was one attempt to work around this problem.)
The ASI vs. Feat choice in 5e also has this problem. And even within Feats it's hard to choose the non-combat ones, or even the non-optimal-combat Feats. (Personally I love Mage Slayer.)
Not sure what the
best answer is to any of these things, but just observing that it's a similar design challenge in all three cases.
I guess one reason I like Shadowdark is that I like its solution to all three (skills, spells, feats/ASIs) problems.