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I am - Ashlands - Menace; In the context of Skyrim's expansions, this narrows the options significantly - Morrowind precluded.
Tracking - Silt Strider - [Paths?]; though I am having trouble making an association, I'm compelled to take into consideration the location of the Silt Strider on Solstheim (Dusty) into the geography pertaining to the riddle's solution.
Quickly Stifled and Flat; though I may only fancy a guess, the subject in question is both silent, and flush with the ground.
[Friends?] - Remember - Anger - [Not sure] - about; I am very hazy here, but I feel semi-justified in associating this combination of words with betrayal.

Though my perception of this rebus is horribly incomplete; putting together what I do know compels me to move my guess in the direction of Ash Spawn, which ambush silently from flat piles of ash, and Ildari Sarothril, Neloth's former apprentice, now undead and seeking revenge for her betrayal (being in that she's responsible for the Ash Spawn). What image comes next? I don't know, but I'm re-directing my thinking (perhaps misguided) toward the notion of vindication and revenge. Thanks for your patience thus far. I'd said before, I'm not too good with rebus.

I'm re-reading St. Jiub's opus, and I think that I'm seeing it all clearly. Each image is a direct citation from a verse in Jiub's Opus. The final image would be in the nature of either "Beaten, clawed bitten" "Knee deep in corpses" or "looking to the heavens before all goes black..." I should have seen this from the very beginning, as the precise Ashland image location that you posted is notorious for Cliff Racers . The Skyrim expansion in question is Dawnguard.


EDIT: Or "About to begin my ascension to sainthood"

Thus began the rise of JIUB!

Three men in a boat addresses one who laments to have every ailment under the sun. Though, housemaid's knee is a common reference to an inflammation of the bursae; in this context, it's referencing a pain brought on by hard work!

"Put money in thy purse, I say, put money in thy purse!" If you want something, you must put money in your purse! A common response to someone who whines about not being able to achieve their goals, but refuses to commit any energy therein.

The final quote illustrates one who throws of their adornment of rags, only to boast a fine new, extravagant garb. Though I was previously unfamiliar with Cap 'O Rushes, I believe that this quote, more specifically, addresses reaching one's goals through honesty and sincerity (juxtaposed with the rest of the folktale).

The antithesis of this progression? I may be wrong, but it seems as though the thieves guild would fit quite nicely in such a context. Of course, I reserve the right to be completely off base on everything.

is it the bannered mare?

belethor's general goods?

ooooooo! Is it the Gildergreen tree?