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Not having the new one (and therefore possibly completely off base), might I suggest the 3.5e DMG II, which has a pretty exhaustive rundown of saltmarsh in it.

Getting someone to do work typically. My entire point is that giving someone more work to do is not in and of itself empowering. In this case, the rules make more work. That does not empower the DM, because the DM always had the power to make a specific assessment, modify dcs or throw the rules...

Nuh uh, with sugar on top. Or, if I actually want a reasoned argument: A beggar and a slave are unempowered. A ceo and a playboy are empowered. The concepts of work and empowerment are not linked except when someone is trying to drive an agenda.

+5 stat makes you a world-champion material natural at the task out of the gate. You are one of the most naturally talented individuals at a task that your race is especially good at. Then you stack on top of that "has studied for their life so far at doing this task" and "is guided by the hand...

Expectation of extra duties doesn't correlate to empowerment.

Which is especially cogent since getting +10 in something is actually pretty difficult in 5e.

So now the skill system requires me to know every skill number on every player's sheet or I'll be labelled a failure? Then why are we even bothering with numbers? This is about dissatisfaction with the skill system, and this is pretty representative of a skill system that just doesn't work -...

Since we're already talking about using the skill system, lets assume that there is some doubt about success here. After all, it's pretty trivial to describe obstacles and then describe characters overcoming them with ease. Doesn't sound much fun though... First up, this is rubbish. It's not...

Don't those things factor into the DC, not into whether or not a roll is necessary? We already decided this is a moderate climb, not a beginner one. We already decided the penalty for failure is something nasty, simply because you're climbing the side of a mountain. But now we need another...

Right... and in this case, our max-level, max-strength, trained in climbing figher (edit - argh, barbarian succeeds automatically!) can feel confident that he can attempt a moderate climb and not risk death! Effectively reducing DCs by 5 feels better than where DCs are currently, because it...

So it's now not actually possible to fall while climbing, is that what you're saying? That doesn't seem satisfactory either!

Because you have pre-supposed that I'm forced to be climbing, obviously the one with a lesser chance of failure... however the reality is that if free climbing was as dangerous as 5th ed makes it, neither they nor I would have chosen to commence the climb in the first place.

Yeah, I made a couple of mistakes. First up I had a moderate DC in mid, secondly I forgot about indomitable might. Take a DC 15 and anyone who doesn't have "you succeed at your check" baked into their class (like a level 17 barbarian). Suddenly both of them fail on a 1-3, both pass on a 16+ and...

That's just indicative of how poorly designed it is. At low level a beastmaster who chooses an animal as his companion is typically worse off than the exact same character ignoring their class ability and simply buying the same trained animal.

Has anyone brought up the fact that in the current edition, skill modifiers usually don't matter? A 1st level weakling with no athletics proficiency will get the same result on a hard climb as the level 20 max-strength barbarian 45% of the time. Would it matter if the proficiency involved is...

My go-to for running any kind of technologist would be the concept that anything that isn't mass produced and consumer focused requires skill to use and maintain. Don't want your grenadier handing out grenades to the entire party? Using a grenade isn't as simple as light, throw. You might have...

My only comment there would be that your low modifier range goes too high, and your high modifier range far too high. Without certain class specific powers (which I would consider to warrant a special case), the biggest modifier you're going to have is +11, and even a +5 represents proficient...

I feel like the problem with 5e's skill system is that the difference between (ignoring class abilities for the moment) the best of the best and the worst of the worst is the difference between a -1 modifier and a +11. If you pick a hard DC, you can't tell the difference between the two on 40%...

You lower your guard, they become more likely to attack you, even potentially at the expense of consequences depending on the character of your target. Otherwise you're going to need some social checks that won't always work, and probably can't be attempted by a wolf.

It's only punitive if you don't tell the player the mechanic before time. As written, it's a niche ability that doesn't get used every round, only when it's important. Personally I might go with "As a free action, you may select a foe and grant them advantage on their next attack against you...