For whatever the worth, one of my controllers exhibits this problem without even dealing with TTS-1.
One of my controllers is a cheap Yamaha YPG-235, which I use mainly when doing piano parts, due to its 76-note keyboard. When just using local sounds, if I trigger a short note immediately followed by additional short notes, it seems to play them all pretty well. If, however, I play in the manner you described in your post, with a short note followed by a held note, it quite frequently will then not play them as two separate notes. That makes no sense, but indeed that is what it does. My better controller does not have this issue. In MY situation, it seems like an issue with the action of the keys.
Just wondering if something like this could be occurring for your situation. What happens if you do the exact same technique using a different soft synth?
Bob Bone