'Pretty bored with the usual gameplay of Skyrim. So i wanted to ask you guys to help me on suggestions for making the craziest skills to build on,
and or with a Master difficulty challenge. Also you can add like limits to this challenge; Like, no fast traveling, for example. Since I don't think finishing the main quest in Skyrim is actually beating the game, I'm going to try to beat it by reaching level 50. I play on console only sadly... so no mods... Please share any crazy ideas, or ones of your own.

A pure thief. Alchemy, Sneak, Pickpocket, Lockpick, Speech, Light Armor. No bows. No daggers. No kills. Have fun.

I might try that, I've done something similar to that.

Become a werewolf, and almost always use it in combat.
Your weapon in human form? fists....

no shouts
no stones
(could make things more challenging)

Have you tried turning off the HUD? That makes just about everything harder in a number of ways.

No crosshair makes aiming ranged attacks more challenging.

No sneak crosshair means you need to pay close attention to NPC reactions to determine whether you are hidden or not. Makes sneak attacks and thievery more challenging.

No compass makes navigation more challenging.

No red dots on the compass makes combat more challenging since you have to pay closer attention to sights and sounds to determine where your enemies are.

No enemy health bars or on-screen text identifying the enemy makes combat more challenging.

No on-screen text makes picking up objects more challenging. No compass icons and no on-screen text makes finding locations more challenging. (I've actually stumbled into caves without realizing it until the loading screen started).

No health/magicka/stamina bars makes keeping track of your health/magicka/stamina more challenging (although I wish there were a way to keep these in and turn the rest of the stuff off on console)

Vampiric Mage

When magicka is drained don't use any weapons but fists.
Can only wear clothes(no armor)
Can only travel outdoors during the daylight hours. (You wanted a challenge)

Pacifistic Illusionist. Only ever use Calm, Fear, Paralyze, Frenzy and Rally.
That's really challenging, believe me. Especially on lower levels.

Another one is to play like a fine noble or merchant or something. Never fight yourself. Use a follower instead, as your personal bodyguard and never ever get involved yourself. Should your follower die or fall to their knees, run for it.
Might be very hard on higher difficulties.

1. turn off hud

2. turn off music

3. turn off kill cams.. or wish you could.

These things will prevent you from ever knowing when a fight is about to start or you're finished (e.g. no more enemies nearby).

Then build this character: Female bosmer, you can only put 1/10 level up points in health, never add anything to magicka.

You can have a bow and fists to fight with.

You can use zero perks in archery or light armor

You are not allowed to cast any spells

I am doing this on and I nearly got whooped by Haemyr's minions..

Master, No HUD, no crosshair, no music, no armour/clothing.

Have only 1 possession, an iron dagger.

Glitch into blackreach using a platter.

Do the crimson Nirnroot quest straight after leaving Helgen.

I like it I might do that with mine. She doesn't wear armor but I will start going out during the day

Wow, that's amazing that I never thought of that yet.

I only thought of it after reading posts on this forum, and even then it took some convincing from folks like Earthlinger that it really is not that hard to play without the health/magicka/status bars. It is way more immersive without HUD. The only time I turn it on is in my house when I am fiddling with my bookshelf.

No saving the game and no turning off the console. Try that.

Use proper grammar

See sig. Crazy hard, if you follow my build (ie. don't take ranger and quick shot), and don't brew paralyze poisons.

edit: I actually haven't used one-handed on the draugr yet, and I suspect that I never will because they will hurt me too much in melee.

Be an Argonian and only travel in water, you can spend an maximum of 3 minutes out of the water, irt

No merchants for buying or selling. Play a leper than no one wants to associate with.

Well, now the OP did say he wanted your craziest suggestions. Actually I can imagine this being kind of a fun way to play, but I would want a mod that kept track of the three minute timer for me and that started the character loosing health if they stayed out of the water too long.

Don't level, stay at level one, no perks.

http://www.gamesas.com/topic/1359145-staying-at-level-1-and-never-level-up/

Does that include khajiit caravans and/or wandering merchants (e.g., skooma dealer)? Hmm, a dragonborn addicted to skooma and treated as such by townfolk -- that's a RP with potential.

I have a Khajiit archer who RP's that he is not allowed into any walled City. He deals mostly with Khajiit caravans, but he also trades with hunters, skooma dealers, peddlers and the traders in Cities Without Walls, like Falkreath, Winterhold Riverwood and Dawnstar. If he needs to go into a walled city for a quest, he puts on a hooded robe and sneaks in at night. If Skooma actually had some negative side effect like it did in Oblivion, I'd probably RP him as Skooma addicted as well, but being that Skooma is healthy and good for you in Skyrim . . .

Play a drunk. You can only wear ragged cloth and most be unarmed (no fist of steel perk, only ragged cloth), you cant do any smithing or enchanting or anything that require concentration or being sobtle (no pickpocket or sneak). You need to have at least one alchohol effect active ever 5 irl minute (preferably more than one). Put all points in stamina to "hold your liquor". No magic or shouts or anything like that (no scrolls).

I'm actually doing this [almost] exact thing! It is so much fun! Good tip about hooded up and sneaking in when having to venture into walled cities.