Honestly, this happens to me for every RPG. (please don't start a rant about how Skyrim is not an RPG) Where I always make a few mistakes that make me want to start over with a new playthrough. For example, in Fallout, I never picked up Stimpacks, not knowing what they did, and I would avoid radiation like the plauge, even though you can't play through much of FO3 without getting at least a little irradiated. For Oblivion, I picked up every piece of junk in site until I realized that useless junk was useless junk. I also tried to kill every innocent person I could find, thinking they were enemies. In mass effect 1 and 2, a lot of people died that I really liked. In Kotor, I picked terrible stats because it was my first rpg

I'm on my eighth because others became unplayable at some point.... PS3.... I wish I would've known to buy it for PC.

I think this happens to everyone. It takes at least one playthrough to figure out things like stats and perks as well as the optimum way to complete quests (as per your liking).

As for me, I didn't realise you could untrap trapped treasure chests until my fourth playthrough. Doh!

You can do that?! Oh well, I wouldn't have done that anyway

Why not?

Oh, nevermind, I thought she said, 'retrap' Yeah, I knew you could untrap treasure chests, but not until dozens of hours into my first playthrough

I wish I knew that you had to focus on more than 4 skills in order to reach level 50, my first character is stuck at level 43 because I only wanted him to use bows, two-handed, heavy armor, and a little bit of sneak.

Yeah, focusing on only one playstyle really causes you to stop leveling at a regular pace once you hit 25ish. Caused a helluva lot of grinding for me to hit that master achievement.

For me, part of the fun is the discovery. With an embarrassing amount of hours logged, I'm still discovering new things.

I know what you mean, but I'm talking about mistakes you made on your first playthrough that seem silly now because you did not know the mechanics

Things you wish you knew in your first playthrough...

That if you try and Sneak attach a Jarl, it won't turn out so well... and that the Housecarls are hard-asses for a level 5 character...

Things I wish I knew on my first playthrough:

Dont waste perks on the lockpicking tree.
Dont waste perks on speech
Get married ASAP. That 100 gold per day will add up very nicely.
Dont try to buy the house in Markarth unless I have enough money to do so.

That is like me.

For my first time, I wish I'd have known that I did not have to follow Hadvar. I did not notice the quest thing pop up and I just followed him. I have followed Ralof every time since then.

I wish I had known that the weapon based perks in one and two handed did not do what they said.

I'm still on my first playthrough.. I'm going to be bored on the my second so bad lol.

I wish I had known that picking up quest items would bug the questlines. I had a character begin a hunt for the bodies of the missing group of Apprentices at the College of Winterhold, but the entire questline was removed when I was about to have it completed
The starts of Daedric questlines really threw me for a loop when I had a character visit Markarth. My character who visited Markarth was helpful and obsessed with the Dwemer, I left the Reach and Markarth with a bad taste in my characters mouth, but I had no idea about the fact that there was a Dwemer Museum and quests inside the keep that were not related to Daedra . The gear I had aquired was almost worth the ick factor, Namiras' Ring, Armor of the Old Gods, Mace of Molag Bal and Spellbreaker.
I thought that Lod was looking for the Stray Dog until December.

Without a doubt the fact that you could "fail" a daedric mission, that was a let down.

I wish I had known that you can't block while dual-wielding. I put a few perks into Blocking before I realized it. I just used the Oghma Infinium to 'recover' them.

One thing (among others) would probably be knowing what certain items are needed for quests.

I've heard people mention this quest, but I've never come across it.

Don't half-ass skills, either go full magic or full attack, as you lose too many perk points this way.

Talk to someone named Arniel Gain, (or something like that) in the College of Winterhold, you may need to complete the college questline, or at least a part of it.

You can fail a daedric mission? Which one? Ive done all 16 twice and never failed one. I have defied the Daedric lords, but I always complete the quest

However. specializing in many different skills is the only way to get to level 50

However, getting to level 50 is only worth it if you want the achievement in my opinion

I'm sure I've talked to him trying to get quests out of him - he's the weasely necromancer guy, right? What counts as completing the questline? I'm Arch-Mage on both characters, but I've dinked around a lot more on my chick assassin. Still never got it on either. o.O