Is it better to kill Astrid or not?

As a long-time Elder Scrolls enthusiast with over 200 hours across multiple playthroughs, I‘m often asked my take as a Skyrim expert – should you kill Astrid during your first encounter or proceed to join the notorious Dark Brotherhood? It‘s an impactful decision that dramatically alters gameplay, so let‘s dive into the key ramifications.

Clear Verdict Upfront

My definitive stance – I recommend first-time players to join the Brotherhood and experience their highly unique questlines. The exotic armor sets, Shadowmere mount and access to the Dawnstar Sanctuary base offset Astrid‘s eventual betrayal. Veterans seeking a fresh run can then try destroying the Brotherhood afterwards.

What Happens if You Kill Astrid?

Assassinating Astrid instead of one of the captives sets into motion the Destroy the Dark Brotherhood quest. This adds an alternative avenue for righteous characters by dismantling their operations across Skyrim. Here are the rewards & drawbacks to weigh:

Pros

• Satisfaction of crushing the assassin network
• Great early game weapon via the Blade of Woe unique dagger
• Access and upgrades to the Dawnstar Sanctuary ultimately

Cons

• Forfeits around 9 elaborate DB assassination contracts
• Permanent loss of Shadowmere, the top tier armored horse
• Missing iconic DB gear like Cicero‘s Outfit or the Jester‘s Clothes

I‘ll speak more to the Dark Brotherhood quest quality later. But ideologically, some players may align with the Penitus Oculatus commander who aids your purge. Just know that by killing Astrid you deprive yourself of much engrossing content.

Quantifying the Consequences

To illustrate the scale of DB content at stake, some key stats:

• ~9 major assassination contracts forfeited
• 20+ hours of DB story content missed
• Over 40k in lost gold rewards
• Missed access to 5 notable NPC followers

So killing Astrid cuts off a wealth of activities but does open up destroying the brotherhood. Tough trade-off!

Joining the Dark Brotherhood

Now let‘s examine the aftermath if you reject killing Astrid. While alliance with cutthroat assassins gives some pause ethically, it unveils a gripping narrative. I‘ll summarize standout gains:

Top Reasons to Join

• Intricate assassination plots with elements of infiltration, disguise and mystery
• Chance to become Listener and lead the Falkreath Sanctuary
• Acquire Shadowmere, an armored steed that resurrects
• Lucrative gold from completing contracts like Emperor killings
• Some of Skyrim’s most memorable characters like party boy Cicero

I won‘t spoil events here, but Astrid eventually betrays you in a bid to retain power over the Brotherhood. Yet following her initial guidance ushers in quests laden with lovable rogues, creative kills and a compelling central story conceit I found gripping even after multiple playthroughs.

It culminates with you tackling sinister Penitus Oculatus agents, validating your Listener role. The arc perfectly complements the fantasy of climbing the assassin ranks in a constantly hazardous (and hilarious) brotherhood.

Noteworthy Dark Brotherhood Gear Sets

I would be remiss not to cover some uniquely stylish armor only accessible while part of the Brotherhood’s grisly dealings:

• Jester‘s Outfit – Distinct harlequin style threads
• Cicero‘s Outfit – Worn by your jester ally
• Ancient Shrouded Armor – Lethal light gear
• Worn Shrouded Armor/Robes – Mix & match shrouded parts

These elite stealth based armor sets lend perfectly to assassin builds. Their visual flair paired with useful enchantments or resistances cement joining the brotherhood as rewarding from both progression and roleplaying angles.

The Verdict?

Based on the above analysis of secrets unlocked, gear obtained and stories enabled, I firmly endorse new players to spare Astrid despite her shady nature. Only later on alternate characters should destroying the brotherhood be pursued for its contrasting rewards.

Veteran tip: Even if you plan on killing Astrid eventually, first experience the DB story content organically until betrayal, maxing your rises in rank along the way. This optimizes unique items & gold earned before purging them on another playthrough!

So in summary – join the Dark Brotherhood and make the most of their compelling narrative. Assassin characters or those intrigued by shadowy groups can later replay a "lawful good" destroy quest. Evaluating from this open-minded lens hopefully helps guide your pick between these fateful options when meeting Astrid for the first time in that abandoned shack.

And if you still remain undecided – flip a septim! Good luck and happy assassinating!