Massey Hall is charming in an intimate venue way. It is heartwarming in the heritage and history way. The sound is nice, the building is in good shape for its age, but there are a few things that keep me from giving MH a better review.
During my recent visit (for a public speaker not a musical act) I asked if photos were permitted. The usher assured me that yes, photos were allowed, but they would appreciate if I could wait until the "Question and Answer" period to take my pics. Of course, I don't want to disrupt the performance so I wait patiently. When the time comes, I pull out my digital SLR (standard, no fancy lenses nothing) and proceed to take a pic, while hundreds of flashes are going off around me. Within milliseconds I have two ushers telling me to put my camera away and that they have a "policy" of no flash and point and shoot only. What gives? I wasn't using a flash at all (everyone else was) and my SLR IS my point and shoot.
Secondly, they take cash only. Meaning, copies of this speakers signed books which are not cheap, merchandise, a bottle of water (soo hot in there) or some drinks for your party.. you better have brought cash with you. No merchant machine of any kind in the building.
The seats are old and tight, yes and can get claustrophobic, even for a tiny-ish person like me. Mind you the theatre was full and I had people much larger than me on both sides. You might want to get an aisle seat.
No washrooms on the balcony levels, go before the show.
Overall I like other Toronto Venues much better. Roy Thompson Hall, Elgin & Winter Garden for example, I adore.