What router and merlin version are you running? I've got iPad and two iPhone 6, Mac Mini and Macbook and no issues using iMessage with my router. Are you using OpenDNS by chance?
I always can send if the internet provider of the receiver is not Videotron.
Step brother
LTE (Bell ou Telus) to Vidéotron (wifi) : don't work
Vidéotron (wifi) to Bell (wifi) : OK
LTE (Bell) to LTE (Telus) : OK
Vidéotron to LTE : OK
Aunt
Vidéotron (wifi) to Vidéotron (wifi, Asus router) : don't work
LTE (Telus) to Vidéotron (wifi) : don't work
LTE (Telus) to LTE (Telus) : OK
Vidéotron (wifi) to LTE : OK
Uncle
LTE (Telus) to LTE (Telus) : OK
Vidéotron (wifi) to Vidéotron (wifi, D-Link Videotron router) : Work
Friend LTE (Telus) to LTE (Telus) : OK
Vidéotron (wifi) to Vidéotron (wifi, Cisco router) : Work
Wife
LTE (Rogers) to Vidéotron (wifi, Asus router) : don't work
LTE (Telus) to LTE (Rogers) : OK