I find it infuriating that the map tells me that I have cleared a dungeon. Does this reset after 30 days?
I traveled to a small town, in order to question some guards, but they got killed by a dragon. If I wait for 30 days at my house in Whiterun will they respawn?

What was super cool was that right when I absorbed the dragon soul, a passing Stormcloak party all ran down to the river and made some comments that made me feel pretty cool. The guards did not make it though. They will come back, right?

Most dungeons will respawn after 30 days.
Generic Gaurds respawn, named NPC's stay dead. I think waiting in the town for twelve hours may allow a different shift of gaurds to wake up? Riverwood does not have a Barracks, but a town like Ivarstead does. Dragonbridge might have a Barracks,too?

Seem the random dragon encounters appear faster when you fast travel, 1% of the time i do, the rest i walk or ride everywhere... downside is, current playthrough, it has been literally weeks since my last encounter with anything larger than a sabre cat.

It is, at Dragonbridge. The ash piles say Imperial Guard. The dragon ashed them. I AM looking for generic guards right?

So, that "cleared" crap goes away?

Also, I have a MQ question. My guy is, a pretty good guy. I had to pass a speech check with some dude name Brynholf to avoid having to deal with his scheme to steal something from someone. (I was looking for some guy named Esbern, who I have since found.) And I was forced to do it, because I failed the speech check. And i got caught, and got fined. And brought dishonor to the Companions. How can I tell if I will fail or pass a speech check? Now he realizes that I svck at stealing so he's helping me anyway, but to force me to pick a lock and steal something....

and....

I found a strange gem, two actually. I'm to bring it to an appraiser. Who I failed another speech check with. I have 40 in Speech, with my level 25 character. Now I have to do a thievery job for some guy, before he will appraise the gem, which I have two of, let me remind you, so I can drop them. I don't want to do a thievery job.
How do I get around this?

Hm you might have just answered one of my mysteries. It's been some time that I've been puzzled reading all those posts about dragons killing merchants in bigger towns and that being a problem, where at the same time in all the hours and characters I've spent with in the game, ever since I bought it I have never ever had a single dragon attacking while I was actually in the city. Killed probably hundreds of the random ones out in the wilderness, and had 2 or 3 spawning near Riverwood, but have absolutely never seen them even close to an actual city.