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.
Just learned something new and it’s so obvious. Thanks @lgaetz.