These devlogs are great! I really appreciate your insights and I don't think there's anything wrong with spending lots of time planning your project. Plus you've got really good inflection in your writing, making it pretty engaging to read!
Something that I really like in games is adaptive difficulty. I think the most prominent example of this in recent years was Elden Ring, where they took the challenge of a souls game and allowed players to make the game (much) easier by farming up. Elden Ring can be either the hardest or easiest souls game, depending on your gear and level. I think vitally, the player is rewarded (the game is LESS tedious) when they choose the high-difficulty option. This is the opposite of what you mentioned with Skyrim...
Hard to implement for sure, but totally worth it!