A useful bit of ihttp://www.uesp.net/wiki/Skyrim:Bounty_Quests. Follow the sub links on that page. Generally, lack of bounty quests being given has happened to folks when they either have one in their journal that they haven't completed for another hold OR they've cleared all the related areas as shown in the tables on the pages in the UESP. This requires waiting X number of in game days for the dungeons/areas to repopulate prior to them being available for a bounty again when asking for work either from a steward or inn keeper. Hope that helps! Cheers!

Well, I've done neither! I have no more bounty quests to do or turn in, nor have I cleared all the bandit dungeons, since I've only done the areas around whiterun and falkreathe, and dawnstar wouldn't give me one even though I haven't done a single dungeon in the pale!

The pale is a bit unique if you follow the link for it you will find that it has 3 radiant quests, one is from Kharjo, one to rescue your loved ones if married and the other actually starts at the dungeon itself, so you won't get a bounty quest per se from an inn keeper or steward if I'm reading the information correctly.

I have a similar problem with my current character. I chose enchanting for my crafting skill. Weapons and armor can fall behind early early without smithing. I'm level 38 now and my ebony sword still only does 45 damage. And that's with enchanted gauntlets.

I like it. It makes combat more interesting.

But my armor is too good. I managed to acquire a full set of ebony. I'm probably gonna go back to steel plate or steel.

I've never gotten a bounty quest or a quest of any sort from the Innkeeper in Dawnstar. I've never gotten the quest form Kharjo, and my characters don't marry, so the only quests as far as I know in Dawnstar is the nightmare thing, the quest for the Hearthfire home (which you need to be I think level 22 to get) and that cult guy.

I got a bounty quest from riften (well, technically from karwasten, but w/e), so I'm apparently not bugged. Oddly enough tough, I couldn't get a quest from windhelm (this is proving to be very very annoying).

Oh, and on my way to riften, I ran into a cave bear, I'm level 16 now I think. I thought it was an ordinary bear, which I had managed to kill earlier. It wasn't until I had popped nearly all my health potions that I realized what it was. Then a wolf attacked me out of nowhere while I was fighting this thing. Then suddenly, a flipping giant showed up and killed it! I had to pop all my stamina potions just to get away. I'm never going down there again.

I did clavicus vile's quest, and I admit, I quite liked having someone to tank for me. I was actually kinda reluctant to finish the quest, barbas made a VERY good tank (being immortal and everything), actually thinking about investing in conjuration.

Oh, and I got my flame cloak spell, but it costs more mana than I have. Guessing I'm gonna have to start investing in destruction perks to reduce the cost of my spells, because I don't think I can wait long enough for me to finnally get to the point where I can put decent fortify destruction enchantments on my gear . I'm having a hard time making money because I'm struggling to find bounty quests. Yeah, I could just go out and raid places on my own, but when I try to do that I end up in like a vampire cave or something that's obviously well beyond my ability.

On the plus side, I did upgrade my weapon. I now have a dwarven axe, with a fire enchantment that deals 15 damage, with 28 charges. Definitely an upgrade. Also purchased some steel gauntlets that fortify my one-handed by 25%. I'm definitely hitting harder now. Also, decided to switch my point spread to 3-1-3. Might switch to 4-1-2, since I need to be relying more on my axe than my destruction spells. Think my destruction's high enough now anyway, since now I can purchase spells I don't have the mana to cast.

Y'know, you don't actually HAVE to have a bounty letter to just go out and stroll into a cave or mine and see what's in there... Bounties usually pay very poorly (especially in whiterun). It's the loot you take that pays off best.