I have not verified all the details about what I am saying here but as I recall, discrimination between typing and gesturing involves the following timers:
- Key typing is registered as soon as touchdown and liftoff from the same finger have been detected.
- 400 milliseconds after some finger touchdown, the event is registered even when no liftoff occurred.
This said, modifier chord are not modifier keys, they don't result in any
Shift/Control/Alt pressed-released event sent from the keyboard unless some
opposite hand activity occurs before liftoff.
In your case, it looks like the Shift pressed event precedes the first sent character with too short of an interval. This would explain why it may be missed by the slow input stream (just a guess!). The Shift Key behaves like on a standard keyboard. The Modifier chords are under software control though, as are the Text Macros.
A workaround would be to use some
series of key strokes for those particular macros. Whit these, you will be able to tune the duration of each key-press (up to 125ms though

). You have more on this in the editor help doc under
Working with the Gesture Tree ->
Event Edit Dialog

You may use the mskey utility to monitor keyboard activity involving modifiers, or xev with X Window.
...
mskey is part of IntelliType 5.3