Will freepbx support multiple registrations on a PJSIP extension and right them simultaneously? Also, can an ext be put on hold on one endpoint and picked up on another?
No that does not exist in asterisk or really the SIP stack.
I just tested with contacts = 10 and I am able to register 2 devices and they both ring, but if I place one on hold the other can’t pick it up 
That’s correct. That type.of feature does not exist in the SIP world with asterisk.
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That’s called SLA or Shared Line Appearance and some call it SCA Shared Call Appearance. It works in the freeswitch environment where you can have 2 extension registered multiple times and you can see that it’s on hold and pick it up. It does not work in the asterisk environment. Pjsip in asterisk will allow you to have multiple registrations but will not allow you to have SLA or SCA as it pertains to picking up a call on hold. The parking lot feature works very well in the asterisk environment .
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