Thieves' Guild (Loud and Clear/Dampened Spirits)

Because the next two quests in the Thieves' Guild line dealt almost exclusively with shadier characters, it was paradoxically easier to justify my actions.

Loud and Clear

Loud and Clear boils to corporate espionage and sabotage, and the moral profile of my character doesn't really account for these kinds of dealings (see The Rules of Engagement).  Admittedly, destroying the property of a Thieves' Guild/Black-Briar business partner may not be paladin-like, but there are a few other factors to consider beyond the necessity of advancing in the quest line:

• If done with sufficient stealth, the quest does not demand bloodshed.
• All of the parties involved are willing participants in ethically questionable dealings rather than innocent victims.
• Destruction of a business's property is reversible and open to compensation if need be.

One unexpected side benefit of my earlier procrastination was that my Sneak, Pickpocket, and Archery skills were now high enough that I could actually complete the quest without engaging in battle. I entered Aringoth's house undetected, pickpocketed the safe key, stole the bill of sale, and set fire to the prescribed three out of five apiaries (using my fire-enchanted bow from a safe distance) -- all without battling a single mercenary. 


Dampened Spirits

Dampened Spirits continues the plot of the previous quest; Maven Black-Briar, the Don Corleone-esque head of the Black-Briar Meadery, asks the PC to ruin her main competitor: Sabjorn, the owner of Honningbrew Meadery.  She has an inside man (Mallus) who suggests that I poison the batch of mead Sabjorn has reserved for a special tasting he has arranged with an Imperial dignitary.  The moral quandries here were as follows:

• I didn't know if the poison was lethal.  Given Maven's ties to the Empire, I suspected that the poison was meant to nauseate rather than kill, but I couldn't be sure.
• I was again helping to ruin another neutral NPC's business.  I should point out, however, that my interactions with Sabjorn prior to poisoning the mead indicate that he is both dishonest and mean, and therefore a more palatable target than the truly neutral Aringoth.
• The Honningbrew Meadery lies just outside the walls of Whiterun.  As I had feared earlier, I was now engaged in criminal activity right outside the gates of my favorite city.

As in the previous quest, I decided to complete the objectives, despite my misgivings.  Fortunately, I was right about the poison; Commander Caius got sick, but recovered fast enough to arrest Sabjorn on the spot.  The business itself survived with Mallus in charge, but I still felt apprehensive about any further Thieves' Guild involvement in "my" city.

Did I forget to mention that I poisoned an Imperial Commander?

By now, my actions have clearly led me out of Lawful Good territory.  While my original definition of Lawful Good in the context of Skyrim may be arguable (e.g. killing and stealing from enemies is morally justified), I was now destroying the legally-owned property of essentially neutral characters in order gain a position in an important faction.  At this point, Lothar Ironfoot had taken a pronounced turn toward the Chaotic.