You're not a mind flayer, I mean mind-reader. What better way than to actually speak to your D&D players and ask them these questions.
Over the last few months we’ve been running 3 games a week with a new tool, FoundryVTT. While Foundry is a great tool out of the gate, one of the impressive things about it that sets it above things like Roll20 and Fantasy Grounds are the Modules.
This Foundry VTT guide explains how to get started loading up a map with custom assets and tokens on a fresh install of the Foundry virtual tabletop.
Skill challenges invite absurdity…but “justification” is part of the fun and encourages players to tell a story in collaboration with you.