I asked my favourite AI after all, and I think there are some interesting points in it, so here it is. You may enjoy it more than my ramblings
and I’m not going to claim it’s mine. Especially with the formatting 
Pay-to-Win: An Overview
Pay-to-win (P2W) refers to systems—primarily in gaming but applicable elsewhere—where spending real money provides competitive advantages or bypasses effort-based progression. The term carries negative connotations, though its boundaries are hotly contested.
Core Gaming Context
In multiplayer games, P2W typically means:
- Direct power purchases: Buying superior gear, stats, or abilities unavailable through gameplay
- Time compression: Accelerating progression dramatically beyond what free players can achieve
- Competitive imbalance: Creating unbridgeable gaps between paying and non-paying players
The classic concern is fairness: does money trump skill? Games are traditionally seen as meritocratic spaces where effort and ability determine outcomes, so monetization that undermines this feels like a violation of the social contract.
The Definitional Spectrum
Your post captures the central tension well. There’s no consensus because “winning” itself is subjective:
The Narrow View: P2W requires actually purchasing victory outcomes—the final boss kill, the PvP rank, the trophy. Buying gear or boosts doesn’t count because you still need to execute. This view treats games as achievement systems where the journey is the product.
The Broad View: Any monetary advantage is P2W because games contain countless micro-objectives. Buying gold, skipping grinds, purchasing cosmetics that signal status—if it advances anyone’s goals, it’s pay-to-win for them.
The Achievement Paradox
Your observation about “winning but not achieving” highlights something fundamental: extrinsic success can hollow out intrinsic satisfaction. You might buy best-in-slot gear and clear content, but the dopamine hit of genuine accomplishment vanishes. You’ve won the outcome but lost the experience—a pyrrhic victory.
This suggests P2W might be self-defeating. If games exist to provide flow states and earned satisfaction, purchasing those outcomes is like buying a birthday cake for yourself and being surprised it doesn’t feel special.
Beyond Gaming
The framework extends to other domains:
Education: Buying tutors or degrees without learning—you have the credential but not the knowledge Dating apps: Premium features might get you more matches (paying to access the game) but can’t make genuine connection happen Social media: Buying followers creates the appearance of influence without actual engagement
The pattern: money can purchase proxies for success but struggles to deliver the underlying substance people actually want.
The Time-Value Proposition
Your Guild Wars 2 example is illuminating. Sometimes payment isn’t about winning but about removing barriers to enjoyment. A working parent with limited gaming time might pay to skip tedious grinds not to “win” but to access the parts they find fun. Here, money buys access rather than advantage—though critics would argue that’s a distinction without a difference if the result is progression.
This introduces market segmentation: games increasingly serve both traditional players (who want challenge) and convenience-seekers (who want results). The tension arises when these groups compete in shared spaces.
The Broader Philosophical Question
At its heart, P2W debates ask: What should be purchasable? Society accepts buying time-savers (dishwashers, ride-shares) but balks at buying achievements (degrees, military honors). Games sit awkwardly in between—they’re leisure products you pay for, but their value comes from creating non-monetary challenges.
Your post’s insight about the paradox of achievement is the key: true “winning” in games might be fundamentally non-transactional. You can pay for outcomes, but not for the feeling of having earned them.