How can an announcement be repeated 2 times than hangup ?
There’s no repeating number field in announcement, just button to be pressed to repeat.
Any workaround other than play announce 1 with destination → announce 2 (with same recording) with destination hangup ?
None ? 
Doesn’t seem like that’s an option outside of writing a custom context.
Maybe send to an IVR, and have the failed destination set to terminate the call?
maybe use sox to concatenate custom/announce1 with silence/5 with custom/announce1 into /custom/announce2, something like :-
sox /var/lib/asterisk/sounds/en/custom/announce1 /var/lib/asterisk/sounds/en/silence/5 /var/lib/asterisk/sounds/en/custom/announce1 /var/lib/asterisk/sounds/en/custom/announce2
Have the system recording referenced by the announcement include the same recording file twice, possibly with one of the fixed length silence options in between.
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