head to head
Neither is meaningfully harder - they pose close to the same test. The widest gap is execution, and it is a single point.

Optimization · Pure Optimization
Building a team and exploiting type-matchup math against scripted trainers.

Optimization · Pure Optimization
Risk-budgeting resistance actions against historical events and probabilistic crackdowns.
Pokémon LeafGreen Version leans Optimization (Pure Optimization); Through the Darkest of Times leans Optimization (Pure Optimization).
Pokémon LeafGreen Version leans a little harder on execution, though the gap is small.
Pokémon LeafGreen Version
Menu-driven turn battles demand no physical skill
Through the Darkest of Times
Turn-based planning with no physical component
Pokémon LeafGreen Version leans a little harder on reads, though the gap is small.
Pokémon LeafGreen Version
Trainers are scripted; link battles are a side mode
Through the Darkest of Times
The regime escalates on historical script, not by modelling you
Same score on variance - which means the number cannot separate them. The difference is in what each one asks of you.
Pokémon LeafGreen Version
Wild encounters, catch rolls and crits add mappable RNG
Through the Darkest of Times
Raids, arrests and event outcomes roll against hidden odds
Same score on optimization - which means the number cannot separate them. The difference is in what each one asks of you.
Pokémon LeafGreen Version
Type matchups and team building are the solvable core
Through the Darkest of Times
Balancing morale, funds and member risk is a solvable system
A matching score does not mean a matching test. Two games can both sit at 10 on execution and demand completely different things of you - which is why the reasoning above matters more than the number beside it.