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Combination of wait_until rising_edge(clk) and wait for is most likely not achieving what you want.

I see two problems why the expected waveform (upper picture) isn't achieved:

1. wait for is blocking the whole process. Alternative cases aren't evaluated before the last active wait for has timed out.

2. your code has no means to generate a specific signal only once, it's not corresponding to expected waveform.

I would choose a different approach, delay generated by counting clock cycles. Having spearate timers for each signal, they can be generated independant of other timers. The code will be also synthesizable.