My experience colors my attitude, but I'll own up to being a pessimist. Here's why:
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.
+1. It's not being pessimistic, it's being more realistic. Sure, it's easy to say, Boston will be ready with the given time but seeing from experience, it is much harder to get things going in this city. It took decades to get Fan Pier off and decades for other projects, the MBTA failed to upgrade significantly for decades, squabbling delayed the Big Dig, etc. You can dream all you want but I'm going to base my judgement on past events and those past events just don't look good.
You're not opposed, but you do sound like saying let's not even try. Let's do that 15 year scenario, and 5 years from now, everyone still still say that it needs 15 years more. Those obstacles are real, but in the bidding process, cities don't start 15-22 years before and then make a bid. I'll be honest, I have doubts, unless someone is willing to pour lots of money to pay for a ton of upgrades to infrastructure and thus sidestepping the issue of construction and politics in financing, Boston will have a hard time. However, Boston is still regarded as a world class city with an international name. If Boston thinks big, it can think big.
To propose that Boston should go for an olympics for 2028 or 2032 for more time is ridiculous. Cities don't make bids like that, they make bids like this, about 10 years before its time. Many cities fail, but in the course of going through the bid, gain much experience, exposed many weakness, and made alot of promises and even began many projects to improve the city. By the next round of bidding, those cities try again and in much better shape. Prague did that for this round of bidding. Beijing did that (though controversial Beijing is) too.
Realism is a fine viewpoint, but realism will not bring change, just learn how to work the status quo. Realism works well in many fields, but if you want to see Boston be a city that can host an Olympics, be a city that can build and maintain a decent transportation system, a city that can build skyscrapers like it used to, then to have that mentality, it need to act like such a city even if it fails in the end. A realistic view will not foster that mentality, just assume this is permanent, but that will never get us an Olympics or even a subway that doesn't break down everyday.
No matter the outcome of Boston's bid for a 2020 Olympics, Boston will come out stronger. If Boston is to retain its status as a world class city, we need to continue to think big, even if this city have not in a long time.