I feel like there's some confusion here. One of the great strengths of the d20 system (D&D 3.5 and its offspring) is that the DCs are pretty transparent. Not that they are all set ahead of time, but that you get a really strong sense of where they all end up. There's that handy chart in the DMG that gives you examples.
So, I as a player and a DM "know" what that a DC 35 check is fantastically difficult but also fantastically impressive. It's like Aragorn (film version) tracking orcs no matter what or the smooth talking halfling talking his way into the king's treasury. So, if I want to build the greatest tracker in the land, I know he needs a Survival modifier of +20-25.
That also informs what would be "trivial" for my character -- as opposed to trivial in general, like buying bread -- a tracking DC of 20 is trivial since I'll always make it, setting aside other mods.
So ... ummm, what's the problem here? Furthermore, things like Skill Mastery (an ability I really like for these purposes), lets you raise the bar on what you'll auto-succeed at without necessarily making you better at the skill.
Now, if the DCs aren't transparent, which is the case in a lot of game systems, then you end up with complete confusion. The player things "I'm the greatest tracker in the land" but then gets flummoxed when the orcs evade him. But, when things are working right, then that player thinks there's something exceptional going on, something along the lines of "these are no ordinary orcs" or "they have magical aid."