I set out trying to prove a point this morning that I'm not just a miserable person (which is only moderately true), and that turned into a thought from the invaluable MLBFarm on how the organizational win percentages compare to the big-league club's win percentage. So let's compare, and let's start with 2005, because why not.
(Year: HOU / MiLB)
2005: .549 / .503
2006: .506 / .553
2007: .451 / .460
2008: .534 / .399
2009: .457 / .426
2010: .469 / .435
2011: .346 / .408
2012: .340 / .527
2013: .325 / .568
So this should conclusively prove that the worst time to be an Astros fan, overall, was 2011. Both the ML team was laughable, and the minor-league system was awful. But holy crap, that 2008 system? .399 win% across the entire system? Jeebus.
The 2008 system had one Top 100 prospect at the beginning of the season: J.R. Towles (#53). After the season? They had one Top 100 prospect: Jason Castro (also #53). Only the Venezuelan Summer League Astros were over .500, at 37-31. The other teams?
DSL Astros: 20-51
Lexington: 45-93
Tri-City: 28-45
Corpus: 55-85
Salem (High-A): 56-84
Round Rock: 64-79
Greeneville: 30-36
VSL Astros: 37-31
In other words, the 2013 Corpus Christi Hooks won more games by July 16 than they did in the entire 2008 season.