How can i work around consecutive skill checks?

If you have a/are the Barb pc in your party with a 3 wolf moon shirt, here be spoilers.

To spare unessential detail, I want to have various obstacle course elements on the "battlefield" of my upcoming combat encounter. Specifically, this kind of idea. except mud pits are replaced by sticky tar.

It is not mandatory for players to engage in these things, but may be chosen for strategic reasons by the PCs &/or opponents.

There are too many to require a skill check all of the time, and I don't think that would really do the variety of the obstacles justice. Similarly, treating it all as difficult terrain sounds lame and less fun.

I want the PCs (and the opponents) to have the option to use the structures strategically, not just as a million skill checks