Thus far I have stayed mainly in cities using caravans or riding frost to and from cities and staying on the roads/paths. I'm in the thieves guild pretty much doing odd jobs and nothing else, picking up the very occasional misc quest along the way.
So far I'm having a pretty good time. I've gotten a couple of improvements for the Guild, which I've never done before. I've just been stealing, looting, training, what-have-you. I'm sure I will get bored eventually and either start a new character or have to branch out wit this one (after completing the Thieves guild most likely).
Any suggestions for keeping a character like this fresh? I've avoided most quests that send me to ruins or bandit hangouts, because I really want to get my stealth up to where I can ghost most areas (I've only put one perk into the base of the Stealth tree, have assassins blade [but am not using improved weapons, just a Skyforge steel dagger and imperial bow], and Muffle. Other than that don't have many combat skills. That's what the Beast Form is for, for when I get in a jam and have to fight my way out.
Note: I am getting better at mounted archery, which is tough without a crosshair.