I'm interested in your take on Skyrim, since I'm still actively playing Modbliivion (a heavily modified version of Oblivion). What are Skyrim's strengths or weaknesses versus the previous TES entries, especially Oblivion? (Bonus points if you've also played Daggerfall and/or Arena

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I started with Daggerfall (and later dabbled with Arena but couldn't get past the graphics). IMO, each TES game has been a huge improvement over the previous. Obviously other people agree or they wouldn't keep making them.
If you look at all the responses to this question, there are of course differing opinions because there are different gamer types who play these games. The range that I've seen is from male tweens to retired grandmas and everything in between. So it makes sense that opinions will vary.
For me, I love the improved graphics (even though my 5-year-old once near top of the line computer has to be on low settings and still melts down after 90 minutes of play). I love how the NPCs have what appears more of a natural flow when you talk to them, often move about and continue talking once you've ended the conversation. I love the AI in the NPCs and feel guilty when I drop something on the ground now. I love it that you can make better armor then most of what you find in the world. I like the addition of having a mate. The armor and weapon racks in the houses is wonderful. We've all got stuff we are very proud of, won't use and don't want to sell. The companions are an interesting addition. I've become attached to mine and consider him a friend. I do wish we had the ability to discuss the current quest like companions would.
As with previous TES games, you occasionally get a super cool quest that blows you away with the story. No spoilers here but I've had that happen a couple of times in Skyrim and found myself in awe, frightened and uncertain as to what would happen to me and my companion, and felt like apologizing for getting us into this particular insane situation. Those surprises are part of why I love TES.
On the negative side, they've gone backwards on the journal. With Daggerfall, I had to keep a physical notebook of my quests so I could remember where I was going, what I was there for, and whom and where I needed to return. They seemed to have fixed that mostly with Oblivion although I had wished I had a place to make in-game notes for myself. With Skyrim, the journal is sketchy at best and it's really necessary to keep a physical notebook once again if you want to remember the details of any radient quest for the purpose of immersion. The horses are really bad in Skyrim compared to Oblivion. I FELT like I was riding a horse in Oblivion. In Skyrim, I'm watching a character ride one. Plus they die easily so there's no way to get an attachment to one, name it and make it a companion.
Overall, I haven't been disappointed in Skyrim. I look forward to a $700 video card upgrade so I can play it on Ultra High settings. I got Oblivion on a lower end computer and when I upgraded to my current computer and could play it on ultra high settings, I was blown away. It was an entirely new game. So in a few years, that will happen once again.
And that, OP, is my humble opinion.
Safe travels.