Well, first I thought to be brave and kill it with arrows, as I was standing high up on the cliff it was sleeping under. Of course, the 3x damage bonus didn't really damage him in any big way, so he woke up and flew upwards. As I was between a rock (said cliff) and a hard place (the dragon), I didn't have a whole lot of room to manuever, and the dragons' breath weapon finished me off before I could put 4 more arrows in it.
After the quick load I thought it be fun and try and stab my way through the dragon, hoping my sneaking was high enough.
Turns out, level 66 sneak actually is high enough to not wake a dragon. So I got a new shout power from the altar behind it, and looted a nearby chest. While I was at it, I drank some coffee, did the laundry, did a little dance and made some weird faces.
After walking a circle around the beast and flicking a booger in its face, I decided to stab it, HARD, from behind. Because that is how rogues like it.
As I was dual wielding two nice self made daggers, I did a power attack-ish move, hitting the dragon three times in quick succession. Turns out dragons have a hard time waking up, so all three hits were considered sneak/backstabs, hitting for 15x the normal damage.
Before I was able to crap my pants and hide behind a rock, the dragon went limp as I finished thrusting it hard with my dag...
Ok, getting mildly disturbing now.
Anyway, I killed it, Looted it, finished exploring a nearby broken tower, went back to town, claimed my reward, unlocked a new shout and decided to pay the fine folks at High Hrothgar a visit for the first time.
Which was a long trek, along which I got killed because of a Snow Bear.
I killed a Dragon no sweat, but I can't handle a goddamn bear.
Funny thing is, the city where I got the bounty for the dragon never reported a much harder to fight dragon hanging around nearby (a green Blood Dragon), which was much harder to kill. I managed to kite it back to town, where the guards helped out with killing it. Pretty nice and all, but still a bit weird that they didn't want help with the more immediate threat. Are dragons randomly distributed/spawned across the land?