I have played SKYRIM 2x.

Both times to about level 35 + -

First time I played the basic game and a mage who became the head of the mage college(visual mods only)

Second time I ended up with an crossbow wielding thief/adventurer who was head of the thieves guild

I have all game expansions and love the SKYRIM REDONE mod and other visual enhancing mods

I tend to stop play when I feel I have gotten the upper hand in gameplay.

I am asking for:

Ideas and perhaps direction on a new character.......OR some enlightenment /encouragement to push on with my thief/adventurer

Thanks. i really appreciate the great resource of this community and the help/suggestions I know will be forthcomming.

Most of my character's don't get above 50, when I feel their story is over...it is.

If you like the "free wheeling" type, As Arem says " Have you tried mercenary work, it might suit you". I like it as I can stick to one side of the map of the other or even one hold.

I also like doing "Thane of the hold" who's more of a "do everything the guard's don't do". Get rid of bandit's, animal's that might attack travelers...etc. This give's me a reason to go in and out of almost every cave, fort or ruin in a hold.

Either of the above can be played by almost any style of character. I generally have a more stable "family" orientated character do this, don't have to though.

Of course a thief type character is also good for doing DB.... to continue on with him or her.

Just my play style but I like very specific type characters, they don't last as long. But because of the way I play I still have not done all of the vanilla content. On my explorer/Thane/Mercenary types I purposely skipped all Dwemer ruins unless a quest took me in it.

I hadn't done a pure mage lately ( for me that's try to get past lvl 15 with one), I also haven't ever gotten any mage skill to 100 except conjuration ( that was with a battlemage) so I have a pure mage that I am doing CoW and Dragon Born with...or trying DB with her anyway.

I've done one or two DiD characters, not a style I could run every character with, but it is fun.

If you're really brave, shift the difficulty level to Master & start the game with that, don't budge it.

Play without ever walking through the doors at Dragonsreach. You never trigger the main quest, so there are no dragons to deal with.

Be a freee-wheeler, don't join any factions.

Never get a house. Just carry what you own; don't collect stuff. If you get the Steed Stone near Solitude, you can carry more weight.

You could do all of this at the same time....