My experience colors my attitude, but I'll own up to being a pessimist. Here's why:
Timeline It's hard to imagine being ready in 10 years. It would be 1 full year to assemble a team, 2.5 of planning, 1.5 of lawsuits, 2 of replanning, 1 of more lawsuits, and then 1 more to finish planning details. Build out in a year? 15 years to plan and execute sounds more realistic to me.
Momentum A staggering disparity in class, a transient population--some 45% of the city, a hysterical vocal minority with disproportional influence, no cohesive transportation leadership at the state or local level, a broken city planning agency and gutless elected officials at every level should be considered. These are generational issues, not decadal problems to be solved by an Olympic bid. The very geography of the city that makes it a candidate for water events, plus the segregation of what middle class there is, hurts Boston.
Construction Unions would love it (there's our middle class from the edges of the city), but who's footing the bill for infrastructure improvements in Boston/Cambridge/Brookline? Who's paying for the venues and the Olympic village? Western Mass will howl at the moon. I don't see how any governor or the Boston Olympic Committee can overcome that. Not even with Mitt Romney at the helm.
I'm not opposed to the Olympics in Boston, I just think they're not viable. Sorry if that's negative, in your opinion. I just think it's the reality of the situation, in my opinion.