I stayed in a Times Square hotel on business in the pre-Di Blasio era and was pleasantly surprised by how clean the area was—there were no pan-handlers or street people to be found.
It sounds like the new mayor has waved his magic wand on the place—and turned it into the standard Democratic urban wasteland.
Rudy Guiliani cleaned up Times Square, Michael Bloomberg continued Rudy’s policies and then DiBlasio threw them out the window
It's reverting to the mess that it was pre-Giuliani. I recall that after Giuliani cleaned it, removing the graffiti from the trains and the human garbage from Times Square, there was an article in the Times stating how they missed the old sleaze of Time Square, which added such character to the city. The NYT pigs must be happy now that they can wallow in their own filth again.
My daughter went to work in Manhattan in 2000 and so I made a number of trips there until she moved. Had the same experience as you. This was the tail-end of the Rudi years. By 2006 you could already feel the rot start to set back in with Bloomberg.