I find the RAW DC's to be too punitive for "typically skilled", especially at lower levels. So I pretty much use this revised DC chart:
Difficulty Classes for Ability Checks in 5e D&D
I generally don't call for "Very Easy" checks, rather those are the sorts of things that don't require rolling dice, and you can just do. Similarly, if something is impossible, I'm not going to go through the pretense of having a player roll hoping for a nat 20 – I'll just say "that's impossible in this situation." But I'm also of the "fewer rolls, more meaning attached to those rolls" school of thought as a GM.
Easy 8
Moderate 10
Tricky 12
Hard 15
Very Hard 20
Incredibly Hard 25
This approach to DC's means that players who invest in Expertise generally succeed more often on those skill checks, which I'm ok with.
One way I arrive at the exact DC number is I'll count up the narrative "downshifts or upshifts", for example: Climbing Out of a Well.
OK, start from DC 10. There are clear handholds and some uneven projecting stones, so I downshift to DC 8. But it's a sheer surface, no slope, so I upshift back to DC 10. It's slick, so I upshift to DC 12. There is no light down here, it's nighttime, and the PC doesn't carry a light source, they do have darkvision, but this is a situation where color-differentiation of algae on the rocks would really help, so I upshift one more time to DC 15.