Hello, some nice construction you have there, both electronic and mechanical.
As to why your latest transmitter does not work, two things come to mind.
The coil L1 and capacitor C2, they should be resonant at around 27MHz.
Are you sure, do you have any electronic test equipment to test that they are resonant at 27MHz?
The crystal. This is specified as a third overtone type.
A third overtone crystal is one which mechanically resonates at three times its fundamental frequency.
If you put a fundamental mode crystal into that circuit it will oscillate at 9MHz, if you are lucky.
JimB