Thanks to my partner, I was able to give this game another shot. Good news is that I like it better, bad news is that I still think Oblivion is the better game full stop.

So for context my only exposure to Skyrim was the base game on the PS3 about a decade ago... a decade... crumbles into dust
Many people regard that as the absolute worst version of Skyrim. My god are those load times patience testing. They occur everytime you enter any area (including merely entering and exiting a shop), and the game was as stable as having a game dev job in the western AAA market. You get one of the many crashes and it takes forever to load that last save. Despite all that, I put well over 50 hours into Skyrim as it was the new and exciting game at the time; especially since I loved Elder Scrolls IV Oblivion so much and wanted to fight dragons and have combat that made you feel like you were swinging hunks of metal instead of plastic cosplay swords. Well I got all of that and then some, at the cost of having a manga on standby every single time there was a loading screen. I read and reread so much Naruto and '+ Anima' during those times, that version of Skyrim is dire and should not be approached by any circumstance.

I actually did briefly get Skyrim on Steam last year during my Steam Deck high, but I got second thoughts and returned it even though it was on sale. I wasn't sure why at the time, but I think it's because I could not remember much about Skyrim. I won't say Skyrim is soulless by any means, but so many changes they made in comparison to Oblivion I feel are a step backwards or make the game less memorable.
Fair warning I'll be comparing the two games a lot.

Apparently people got really distracted in Oblivion when talking to a NPC paused the world around yourself as it zooms in onto the NPC's face. Have to say I don't like the alternative where instead Skyrim NPCs just stand in place and are often not taking much, if any, screen real estate (unless you talked to them from very close by). Doesn't help that the NPC models and designs lack a ton of personality that Oblivion had, even if the latter is bordering on the uncanny valley nowadays. Because Oblivion zoomed in on the faces, they had to make the NPCs very expressive and emote with every dialog piece. Their emotions would even change depending on your reputation and affinity towards the player (which can be further changed with bribing, persuasion, or charm spells). Plus nearly every character in a town or city has their own name, their own personal greeting when you first meet them, and you can always ask for rumors they've heard that can lead you to new quests or hints. Not saying Skyrim has none of those characteristics, just that Oblivion has a lot more intimacy with the people you talk to.
And this all without getting into what I feel Skyrim stumbles the most at: Quests. Especially the quest lines involving the factions. Let me paint a picture: you are a mage in Cyrodil. You wish to further enhance your magical prowess, and to do that you want to be enrolled in the Arcane University of the Mages Guild. In order to do that you will need a written recommendation from (almost) every city's Mages Guild. These quests range from pulling a silly prank, recovering a stolen mage staff, thwarting a powerful mage whose also a highwayman with the help of some mage guards from the university, and even discovering that necromancy, that has been banned in this country, still has its claws steeped in the Guild's hierarchy. You have to do so much just to get into the most prestigious and sought-after university any mage would love to be a part of.
In Skyrim you cast a single spell that the gatekeeper gives you and your in the college. Even in context of what the college is, that is so lame and boring.

And that was just one example. The Dark Brotherhood no longer has interesting bonus rewards for completing assassinations in a unique way, the Fighters Guild often has you deal with randomly generated radiant quests for half it's content, and there's not even an arena to speak of. So many quests have such weak storytelling or are extremely basic to complete, not to say Oblivion was perfect in the latter but the former is a key strength of Oblivion to me. To be fair, not every quest is dull. I like how you join the Dark Brotherhood, their version of the Fighter's Guild has werewolves (which are still pretty undercooked from a story perspective, but werewolves are cool), I like how the Daedric god quests can be anywhere in the world instead of at designated shrines, and the conspiracy quest in Makarth is always a highlight with how it changes the rules of how the law normally operates in towns. Still I had to struggle to remember Skyrims quests, whereas I could describe so many of Oblivion's quests off the top of my head... Going inside a artist's painting, calling out the corruption of Cheydinhal with their extreme taxes (which also makes bounties in the town higher till the quest is completed), buying a house that turns out to be haunted with a litch in the basement, thinking your hired to kill some rats when it turns out you have to protect them from mountain lions, discovering the origins of the Arena's Grand Champion which makes him so distraught that he throws the championship match and his life, the unmarked quest at the highest mountain in the game where you discover a invisible monster that slaughtered a couple, killing five guests at a mansion while utilizing their personal biases against one another to divert attention away from yourself; I could keep going you get it already.
My disappointment doesn't end with the quests sadly. So many things that did not return from Oblivion I'm still surprised by, or changes that make playing more annoying then engaging. Like, why can I no longer create my own spells? Why were attributes removed so that I can't increase things such as my carrying capacity or movement speed manually during level ups? Why do merchants have limited number of funds and require me to keep finding new merchants constantly after a dungeon run? And for the love of god, why is the acrobatics stat gone? I love making my character capable of jumping higher then the trees, able to take shortcuts within dungeons and potentially even go out of bounds. Just a lot of fun tools were lost when they made Skyrim and it made playing the game feel far more limiting for a series famous for being able to do what you want, when you want.

And with all that said, Skyrim is fun to play. The way leveling works makes nearly every action feel meaningful. Gold is always in demand, loot can be used for potions, enchantments, crafting, cooking, and smiting which gets you into a mass hoarding mindset. Your consistently working towards something, and growing stronger makes a noticeable difference. Enemies tend to be a lot more aggressive and dangerous then Oblivion, less exploitable A.I. in general (but can still be pretty stupid). Often times though enemies and boss monsters can deal way too much damage and have way too much health. The way scaling works in Skyrim means that there's higher incentives to become strong, but also more frustration when a random dungeon monster has numbers so much better then yours that you have no choice but to leave. That, and the infuriating pre-animated takedowns delivered by the enemies. If you are low on health a enemy can just decide seemingly whenever "Die!" and will lock you into a death animation instantly. It isn't even like it's a grab attack or something, the game just decides to kill you right then and now. The last time I played Skyrim before this was with a mage character, where I didn't invest much into health upgrades. I was fighting this skeleton dragon which was already a tough boss, and I took a lot of damage so I paused the game to fully heal myself with potions. Despite now being at full health, the dragon did an instant-kill animation on my character anyway. Reminder that this was on the PS3 with those grueling load times, and MAN that death was so aggravating that I just stopped playing that character in its entirety. I don't care that these can occur with the player character doing them, these suck so much.
sigh Didn't I say that Skyrim is fun? Well it helped that this playthrough was a sneaky archery build. With the edition of the gane my partner owned I was able to dip my toes into the world of crossbows. I played like it was more of a shooter and it made fighting simple yet enjoyable. I like the variety of crossbow bolts that range in damage and effects. This build especially helped with those dragon fights that are, 80% of the time, just flying in the air. I mean it makes sense from the dragon's perspective, but also I guess get fucked if you are a melee build. But yeah crossbows are cool. I like the perk that allows you to slowdown time at the cost of stamina, able to calmly take out enemies that are making a beeline towards you if you get caught. Stamina in general is a lot more impactful of a resource then in Oblivion, where it affected how often you'd be staggered by attacks and a minor damage bonus depending on how full it is. Using stamina to sprint is a fairly generic mechanic, but if you're in a situation where you have to make a run for it (and you will with how you can randomly encounter powerful foes) then it can get genuinely tense as your stamina rapidly depletes with a angry mammoth breathing down your neck. The perk system is mostly kind of whatever, but it does have a share of interesting abilities that can greatly change how you play the game. The one stealth perk that gives a massive bonus to sneak attacks, but only with daggers, gives that weapon class an interesting niche above others. A heavy armor perk takes the armor rating of your gauntlets and uses that for bonus unarmed damage. Unarmed is not a skill that can be leveled up, but this perk combined with certain races bonus damage with their natural claws can make fun and viable unarmed builds. In fact, that very build was when I first started having fun with Skyrim when I initially played it. Sure it loses viability as the player's level increases, but it's still very silly yet satisfying.
And even though Skyrim is not as much of an RPG anymore, not all of their simplified systems were bad. Consolidating the melee weapon types to just one-handed and two-handed makes more sense then blade and blunt skills, since the former are a lot more understandable in the kind of playstyle they'll offer, whereas with the latter two there aren't slash or bludgeoning damage types in Oblivion that makes a hammer and sword of the same damage values play noticeably different. While speech is very underwhelming when it comes to persuasion checks, combining it with the mercantile skill makes a lot of sense. As Oblivion's mercantile and speechcraft skills were both slow to level up and hardly made a meaningful difference when they did increase. Combining the two allows you to get more out of both while not making things too bloated. I like how bounties are only relegated to each city instead universal across the whole country, which emphasizes how much more isolated the land of Skyrim is in comparison to Cyrodil. The dungeons are a lot more interesting to explore with wider variety of locales, a lot less copy and paste areas (though still not perfect), actual puzzles, and all around greater sense of scale.
Yet with every compliment I have for Skyrim, I also keep thinking about more and more things that bug the crap out of me with this game. Like the menus, I really don't like them. They're too simplistic, boring to look at, and not as intuitive to navigate as they should be. And just... god this game is such a mess to play and write about. I have had sessions where everything is working out and I'm chill, vegging out after a day at work. Just want to play something that ain't too taxing, and Skyrim delivers it's promise. But then I have sessions where the cracks start to get too hard to ignore, and I grow annoyed and bored with the game. For the love of the dragon god, don't play a dedicated mage character on your first playthrough. They are so much work for not enough pay off, just choose a few spells for utility as that's really all you need. And it sucks since magic is so cool in these games but their low armor class, limited magic pool, and lower health doesn't mesh well with Skyrim's design.

Skyrim is cheesy popcorn. Delicious and hits the spot, and then you start biting into unpoped kernels, it gets stuck in your teeth, and your mouth drys from the saltiness. But when its working right its addictive and easy to digest. Just sometimes you want more depth in your foods.

Oblivion Count: 15
Skyrim Count: 24