I think here is the gray area of the definition of winning. Winning it all? Being an above .500 team? Being a consistent playoff team? Being a consistent championship contender? The definition may vary for us, but it doesn't really matter. Whats the definition for the FA's? And for them it will vary as well. We need to find the ones who prefer this culture like River said. Guys who, if they want the big city to party , plan responsibly and they have the money to do it anywhere in the world. Portland is great place for a responsible kid to stay honed and focus on priorities after taking a weekend bender in Vegas or LA or NY, or the Bahamas or whatever.
Plus, like I pointed out in the OP that some of you seem to have missed, the teams nailing the FA's don't have much better weather than us!. Boston? Anyone lived in the NE in winter? Fuck, Ill take the rain every time man. Plus any educated person knows the rain is what makes this place beautiful the rest of the year like Bones pointed out.
The weather cant be a major factor.
I think its the organization, and we just came off of a major change. As good as our organization is, it doesn't provide the stability of an SA or GS ... YET.
Another year or two though with consistent play and low caliber moves that inches us closer, we might just turn the corner yet and build the confidence in these top tiers that we are in it for the long term and winning isn't a momentary thing for us. That's what NY is doing and it is going to fail miserably. It almost always does. Teams like GS and SA think about the long term and we are doing that too. We just need to keep doing it and I think eyes will open up to it.
Patience and persistence, like most things, will prevail.