Hi Glen
Just giving the plugin a test-drive and looks to be working.
on the action "send imsg message (imessageplugin actions)" the select buddy drop down list is not visible when you first select the action. I have to save and reopen the action before the drop down list is visible. The workaround is to save and open the action again, but you may want to have a look at it.
I am also struggling to send a gif or jpg, but not had a great deal of time to explore that yet, probably my error, but will let you know.
Great plugin and keep up the good work - thanks