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The only I reason I said Pittsburgh might be out of my comfort zone is because I never been compared to the other cities. And Imma be all the way honest, I don't know as much about it and on the surface it seems so predominately White that as a Black tourist I might stick out more compared to the other 2. BUT, I adapt very well in other places so don't take that as me only wanting to visit places with a lot of color. My interest is all the way in on Pittsburgh. Can't judge a place until I visit so yeah.
As far as why not Philly? Well me and my Wife already visited Philly back in 2020 and had a really good time while there. One of my favorite trips.
And as far as Southern cities go, I've been to most major southern cities so I don't have any desire to revisit these places on my first solo trip in YEARS.
Granted I thought about going to Asheville, NC and Richmond,VA but other than those 2 I've been to most.
Also I didn't wanna visit a city that me and my Wife have on our bucket list to go so some cities like Seattle, Boston and San Diego will be pushed to the side and we'll go to those on our future anniversary trips.
Makes sense. Hope you have a good time. Let us know how it goes.