I've seen some really in-depth guides and character builds focusing on certain play-styles, but more often than not I see people complaining about how there is no challenge once you reach the height of that character's specialization or you become thoroughly bored with the fact that your character lacks variety. I figured nobody would mind if I tried rectifying that - better to have failed and have tried than to never have tried at all, right?

This is my take on a jack of all trades, master of none themed play-style. It's good for challenging the player as well as roleplaying, if you're into that.

Outline

• You must invest a minimum of three perks into every single skill, meaning 55 out of 81 perks would be distributed evenly leaving you with only 26 perks to spend.
  
• You must invest perk points into a minimum of two perks in each skill tree. This prevents you from adequately mastering any skill and goes rather well with the theme.
  
• You cannot fast travel, but may still take carriages. Adds a bit a realism as one does not simply teleport from one place to another (though sometimes I wish I could), and keeps a bit of immersion if you happen upon random encounters during your travels, which is part of the challenge.
  
• You cannot invest more than 6 perks into any skill. At this point you'll probably want to do a bit or pre-planning.
  
• You may play on any difficulty. If things are getting easy, then feel free to kick the difficulty up a notch. Be warned though - playing on master difficulty should challenge this build even at level 81.
  
• You cannot increase any base (meaning magicka, health, and stamina) statistic by more than 50-point increments until you've increased another base statistic by 50 points. Meaning you can teeter-totter between two bases, but only in 50-point increments at most.

Those are the only guidelines I really have for this template. This should prove to be challenging for even veteran TES players, but more importantly, it should keep things interesting for you. If you want an example of what my build looked like by level 81, here: http://skyrimcalculator.com/#157050

I know this isn't in-depth, but I wasn't really trying to go into great detail. I prefer the direct approach to things. This template is simply meant to provide some challenge and variety for the player.

This is somewhat off-topic, but designing a build around level 81, in my opinion is sort of pointless. I can't imagine getting anywhere close to that unless 1) glitching to it or 2) being miserable with grinding.

50 is far more realistic.

There really isn't much point levelling up past 50 anyway. Pre-Dawnguard all enemies stay at the same level from 50-81 mostly. Only if I've done everything else I wanted to in the game would I spend the time grinding to get to 81, I probably will of course, but I'm nowhere near there yet.

I think I've done the Oghma exploit 20ish times now, so I didn't base this idea on the soft-cap. Maybe I should've, because it's like you said - unrealistic for everyone to even want to grind to 81.

Fair point. I guess it just depends on play preference

With my last warrior character I kind of went in the opposite direction. I specialized so deeply it made the game difficult.

The character wore Hide armor (without helm) and used a steel 2-Handed sword at level 54. He used no magic, no enchanting (and no pre-enchanted weapons or armor), no Alchemy, no Guardian Stones, did no Lockpicking, no Stealth, and did not buy or sell to merchants.

He leveled only three skills (Light Armor, 2-Handed, Smithing). I put perks into only those three trees.

I used mods that disabled fast travel and that made carriage travel cost 500 gold so the character was rarely able to afford carriage travel even when I felt like it.