First Playthrough - 134 Hours
Wanted to play as an archer focusing on conjuration magic and alchemy. Decided to not use any fast travel. Resulted in an endearingly difficult first 70 hours as I had many mechanics to learn and even getting between cities was an adventure. It fell flat as soon as I understood the leveling system. It encouraged me to never venture outside my quest route and avoid combat as much as possible, because each level would only mean spongier enemies with extremely sparse returns for the player.
I realized how much being an archer blows ass in this game with the spastic enemy movement, ♥♥♥♥ arrow damage, difficulty in getting high-grade arrows from shop keepers, arrow despawning, and low returns from enemies. Picking arrows up from the floor after facing 3 skeletons in a dimly lit dungeon is more of a struggle than the battle itself. The loot is never worth what I had to spend on arrows, and so if I chose to do a dungeon instead of sit in the fields south of Cherrol picking flowers, I was actively losing money. My bow became nothing more than a vehicle for poisons. I tried to focus more on conjuration, alteration, and destruction, but by that point trying to stack enough willpower buffs to not spend an entire fight running in circles waiting for my Daedroth to hit something while my posions tick away was nearly impossible.
The playthrough really just lost all of its charm and magic when I realized the most effective way to play this game is to barely engage with it at all. Add in the difficulty slider and everything just felt unbelievably arbitrary. I had planned to finish the main quest line, get all Master Alchemy apparatuses, and then go down the Dark Brotherhood questline before stopping. But after about 20 hours of speedrunning Oblivion gates at 200 speed and athletics in an effort to get +13 Willpower sigil stones, defeating Mankar Camoran within 2 minutes, and watching Mehrunes Dagon be defeated in a cutscene, I realized the more I got to know Oblivion, the less I enjoyed it.
Is it really all that much better than Skyrim? One playthrough of both under my belt is telling me no. Both are fine for a while and then become pointless because of the enemy scaling not matching the mechanics or amount of content.