RP is impossible in vanilla Skyrim. If you want to roleplay it's far easier to do it with a pen and paper (like D&D, or just write your stories and stuff) than it is with vanilla/unmodded Skyrim.
The base game is practically still in its alpha stage, and is not that much better than your average steam early access survival games in terms of completion. The game is also filled to the brim with bugs, which the dev after 6 years and like 15 re-releases still have not fixed. Why Bethesda is allowed to pull shit like this is another matter which we won't get into here.
The reason why vanilla Skyim is impossible to roleplay comes with the fact that
- There is almost 0 choices to be made in the entire game. So there is little to no nothing to roleplay to begin with.
- Most of the quests are straight up just dumb with 0 nuance or smarts. So for most people it is hard to roleplay and want to continuously do so in a world where the average IQ even among the elders and the gods in the said fictional world is like 50.
- The base game's perk system actively prevents you from specialising your character. Because in order to progress into higher levels, you have to do everything, which means every late-game character is EXACTLY the same and as 'master of all'. If you don't do that, then you will be stuck with early game mobs/encounter/etc forever. The armour progression is also completely linear, so unless you want to give yourself a handicap in stats otherwise you will always end up with 1 of the 2 end-game armours; one for heavy armour, the other light armour.
- The armour and weapon design is just bad in this game, this goes for both quality and diversity. There's only like 10 armour sets in the entire game, weapons have a bit more but it isn't helping, and most of which look horrifyingly bad. And as said, the progression is completely linear, there is no "this and that armour" there is only "better and worse armour"; while there is enchanting, they are typically minor with the sole exception of robes where it plays a slightly bigger role due to emphasis on spells. On top of it, the greatest sin here is that they didn't even bother separating torso armours from leg armours, WHAT? So there's that for roleplaying.
- The magic and shout system is HIGHLY unpolished and limited in the base game, and most things in their catalogue are straight up useless (I'm looking at you, fucking invisibility spell, that the only thing it ever does is just turning your character model invisible TO THE PLAYER ONLY and not to any enemies or anything). So that's a problem.
- Melee combat is k, but it's barebones and the animation is abysmal to look at and execute even for a 2011 game. Bow gameplay is fine, however.
- The stealth mechanic is completely broken in the game, and is entirely non-intuitive, nor is the game designed with any forms of intuitive stealth in mind. Stealth is just a stat-check. Once you get enough level on it, pressing the crouch button makes you a god of shadow that no one can see even if you are crouching right in front of them in broad daylight. You also can't just roleplay your way out of it too, because save for a couple specific locations, none of the locations in Skyrim is even stealth-friendly, so you are forced to just sit and watch your character crouching in the middle of the pathway while all enemies can not see you even if they bump into you with no other way to approach it.
- The combat, in any difficulty setting above the easiest ones, is completely revolving around stat-checking with button mashing and fighting with your inventory. The reason being, the game barely has any strategic element to its combat, if any, hence difficulty presents itself completely in higher damage and toughness in the enemy mobs which requires more mashing than they would otherwise need for lower difficulty settings; this is then combined with the fact the game's combat menu is incredibly unintuitive and you're frequently required to pull out the bag (doing so pause the game) and run through your potions and food reserves for heal and stuff, before going back to real-time combat and mash buttons; Repeat. Any "strategy" this game would have, is not an interactive experience between the AI and the player, but rather it is just exploiting the game's barely existing/functioning AI; hence I thus consider this game having little to no strategic play by design. The problem is that this kind of "combat" may have worked for Runescape or other very old RPGs and whatnot back in the day especially when it was also top-down so people could stand it, but in a first or third person action game in modern standard that is just immersion breaking to actually play.
- The bugs. Oh my fucking god the game is filled to the brim with bugs. They clearly never bothered to tested it AT ALL because even just bugs in the main quests that breaks the entire thing are still unfixed even to this day; and players are still required to either mod or use console commands to progress the game's main quest alone; this is not counting the documented tends of thousands of bugs in the game. That's just stupid, the entire base game is completely immersion breaking if you intend to roleplay because of the countless bugs.
- The game levels with you almost entirely. So you will never feel like you're making legitimate progress in any way besides getting more stuff to put into chests and more completed quests on your logs. Game progression itself is bare to say the least.
- The dragons become a pest and a chore after the first 20 min of the game. Most people actually mod the random dragon encounter off, or simply refuse to progress the main quests to go and see the Greybeards (it's like the third quest for a new character) which by doing that the random dragon spawn will never be turned on, but your main quest will never be completed.
- This one is personal, but I feel Skyrim's map FEELS really small for some reason, maybe that's because most of the holds and settlements are tiny, the distance between them while is cool but there is a lack of noteworthy things in the path since a lot of places are just either samey or make 0 sense (like a volcano section of the map is just 1 river away from the frosted hills) that makes the journey worth remembering hence feeling small, as well as a good portion of the map are mountains and other cliffs and other stuff that you can't legitmately access without glitch-hiking and there's nothing in those areas anyway (save for like 1 instance where they sneaked a 300 movie reference in one of the off-beat mountains) which takes up a good chunk of the map for nothing. The player's map looking like a satellite google earth map instead of a printed/hand-drawn map also doesn't help with the immersion.
- All of the characters are robots, and just repeat the same thing over and over and over. They save for a couple, have absolutely 0 emotional depth or character development, nor do they acknowledge your existence in any way and so they will say the same thing to you for eternity and it just breaks the immersion.
- Coming in full circle with point 1. There is almost no consequence in the entire game. You don't get to make any choices. For instance, they don't even bother adding in limitations for joining factions, even for those that are supposedly in conflict with each other. You can literally be the guildmaster of every guild and the thane of every hold and the game won't give a damn. The base game is effectively a theme park ride, it's designed to be such, and it makes the thing incredibly hard to roleplay in if not impossible. Hence why I simply said it's probably easier to do it with pen and paper (like D&D, or just write your stories and stuff) than with Skyrim, because at least the pen and paper don't actively disturb immersion at every corner.
So if you have to RP in Skyrim you have to mod the game, and by that I mean you have to SERIOUSLY mod it, change it into a completely different game to do it. Or better yet, just don't play the game. When the fully released game requires the players to develop, fix, add content to a game, and do a community project to change it completely into another better version of the game to even be remotely considered enjoyable from its HIGHLY unpolished and unfinished state, it simply doesn't deserve to be played, especially not with such dedication.