Well, I am a new "convert" ,so to speak, to the Hotel Pennsylvania. For many many years I had stayed at another hotel in Times Square.
It can be a little gringy, but usually you can get a good price. For my first stay I booked it on an online service at $89 per night.
Let me say this about it: though old and creeky, at no time have I felt unsafe in it or in the immediate area.
FWIW I was there during the Great N.E. power blackout of August 14, 2003. It is was one of the few hotels in which one could access one's room, if you did not mind climbing 13 floors in the dark. The little gizmos into which you insert your card to enter the rooms was actually working! That must have been one of the few electronc devises in the whole city that worked.
The next day, I was in the Times Square area and saw my old hotel, and it looked like its people had spent the night on the street.
Glad I was in the Hotel Penn. Stayed there now two visits in a row. I had no complaints with my old hotel, the Paramount on 46th Street. Just changed over to the Penn because I was going to meet with Alan and do some train riding and it seemed more convenient.
Turned out to be a smart move for more reasons than that. The room was hot and stuffy but being such an old building, you could open the windows, a blessing in disguise.
The Glen Miller Orchestra first played "Chattanooga Choo Choo" (I am from Chattanooga, for those newer board members who do not know) in its ballroom, so that is is part of the history Alan referred to earlier.
Guess that ballroom was one of the places we had to find our way through the dark in August 2003. It was probably more fun when GLenn Miler was there.