So yeah I am done, had enough for now, just not having fun anymore. So I am playing what is mostly a heavy armoured 2 hander weilding warrior and due to the limited perks and a system that punishes you for having too wide array of skills I decided on focusing more on the skills and perks that support this play style, so that means no bows, no stealth, no pickpocketing and that sort of thing and while I managed to suffer through the backpedaling Draugur mages who backpedal faster than I can move forward while swinging a sword and the [censored] dragons that wont [censored] land and go "trololo you need a bow to defeat me" even though I invested no perks or skills into it making any damage I do with a bow [censored] useless I finally run into the straw that broke the camels back.
So as I am going through the main quests I run into a mission where I need to infiltrate a Thalmor embassy, oh joy just the mission my character is totally unsuited for. So I go along with the motions, and after the Wood Elf leads me out of the party room I am supposed to somehow sneak past all the Thalmor guards and recover the evidence, problem is 1) my sneak skill is pitiful so as soon as I enter the same room as a guard he notices me making it impossible to sneak through, 2) even if I could sneak up to a guard trying to stealth kill him is impossible due to the fact that any damage I do with a 1 handed weapon is pitiful even with the sneak bonus and dont get me started on my bow damage, so my only option is to go bezerk and make as much noise as possible while I slaughter everyone in the embassy and while I know that this is still a viable option to complete the mission it just feels so [censored] stupid and counter intuitive to the initial mission plan, why bother with sneaking me in with a phony invitation if I am just going to turn the mission into a [censored] bloodbath? Why dont I just kick down the [censored] door and do it that way?
Anyway dispite how [censored] stupid the previous mission was I managed to put it out of my mind and slaughter my way through the embassy however then I come to the next mission where I need to head to Riften to get some information about the whereabouts of a certain someone, however upon asking him for the info he says "hey how about I create a diversion while you steal something and slip it into somebodies pocket with those pickpocking skills you dont have?" and I just decided thats it, I have had enough, of course there is the option to bypass the mission with the speech skills I dont have however I feel at level 27 it may be a bit late to be training the skills that I need to pass the main quest and I cant be bothered starting a new character just yet, so I am taking a break and might wait for the Construction kit to come out before I start again, who knows perhaps there will be some cool mods released by then and perhaps Bethesda will release a patch that fixes a few of the problems with their [censored] UI.
I used to rant and rave about how the world wasn't how I wanted it to be too until I realized that a lot of my problems were do to the choices I had made in life. Your tale of woe sounds similar. I'm a role-player from way back so I try to put everything into the story-line.
1) Ok, mages and shooters like to backpedal while I close in. One of the Shouts you can get allows you to move forward REALLY fast. Use that and suddenly you're in melee range.
2) My big burly Orc hates Alchemy and casting spells so he buys potions from other people. Not a game flaw, just his style. In the scenario you mentioned I would likely strip down to my skivvies, take an Invisibility potion and do the best I could. No offense but in the movies often the 'sneaky' plan turns into a bloodfest when the big fighter screws up.
3) The next mission you mentioned was an introduction to the THIEVES GUILD! Why on earth would you even TRY to take a big, lumbering fighter type through that?
4) Dragons fly and breathe stuff on you. That's what they do. Not landing is called playing to their strengths. Not learning how to fight one is called being stubborn. Try recruiting a follower with a bow or with spells to do fire-support for you until it lands. Or try using a potion that increases your Archery skill.
Not every character will be able to succeed at every task if they don't at least TRY to step outside their comfort zone. It happens in real life all the time. Over-specialization breeds weakness. Adapt or die.