There are no guarantees that any of these areas will see a resurgence or successful gentrification. It's a hope, maybe even a likely possibility, but not written in stone. Many people have gotten lucky, and many have made incredible gains and enjoyed significant reward from buying housing. But it has also caused a lot of heartache, and can easily go the other way.
When you bought, was it a teardown dump (I'm just using that in a general sense) and was it your only option? And were dozens of other buyers eager to outbid you for it? Did it take very cent you had (and then some) just to get in the door? My guess is you bought what you could afford, as close as you could get to the location you desired, and that the property was reasonably priced based on demand. The surge in market values and desirability were hoped for and anticipated, but probably not viewed as a sure-thing. You are probably just as surprised as everyone else to see where things have gone.
I would also think that living right in the city was still viewed more unfavourably (especially by suburbanites) in the 90's, i.e. less desirable and safe. That's a general view that has softened in recent years as shows like "Seinfeld", "Friends", and "Sex in the City" have helped make urban living look more appealing and exciting.
Again, my concern is that this one type of asset has fostered such desperation that people are willing to spend everything they have to get it, even if it's not what they want or where they want. It's a much different landscape than when you bought, or even when I did. My feeling is it's a wealth swindle, and people are playing right into it. Everyone else can see it happening except for those viewing it from the inside. We are frogs in a pot of water that is being slowly heated. By the time we realize it's time to jump, it's already too late.
