While I never lived in St. Louis, I did live near enough that I went there for weekends away from the small town I was living in at the time. I would rate it 50-50 as far as being a city that tolerates differences. My feeling is that it is a city that trends towards the conservative.
I did definitely get a lot of flack for wearing a Detroit Tigers cap around the city. Of all the MLB parks I have been to (18 so far) it is the only place where some folks went out of their way to give me and my friends a hard time. While that may not translate into their level of trans-friendliness, I do consider it a decent barometer of the cities overally treatment of folks not from there.
St. Louis does have my all time favorite Italian restaurant; Caleco's on North Broadway in downton. Bring a big appetite their portions are massive.