Yeah convincing people to use something else is going to be fun. I'd push for Hangouts since they are currently using Google Apps for business anyhow, minus maybe one of them. I'm glad to hear someone else feel that iMessage is just ungraceful as hell when it fails to send to everyone else.
I guess I'll push for them to use Google Hangouts and see if that makes things any better. It has to be SIMPLE and unfortunately I have a feel that the owner is going to see this as a failure of the Android device.. Which you know what, I seriously think that Apple does this s^&$ intentionally. I think they want the messages to fail to go to Android or other users just so that it looks to the laymen that the common denominator here is the Android user. Which is true, only in that they aren't using some BS Apple messaging app. If they allowed not iPhone users the ability to download an "iMessage" app and sign up for an account it would at least make some form of sense and show that they care. I believe they would rather play dirty. Shame.
I'm going to be really sort of pissed if I'm expected to go get this one Android user, who loves his phone, an iPhone just so they can "group text" when it reality they are just using an iPhone messaging app that is circumventing using MMS.
Thanks for the re-confirmation that this isn't some one off issue. Appreciate it. Ohhh, and I did find lots of posts elsewhere of people having a nightmare of removing them as an iContact when switching from an iPhone to Android, regardless of following the steps to fix it by removing the device from their account, not an isolated incident.
Of course, Google does the same sort of thing. Use Hangouts/Voice as your phone number, and it likes to throw in Google+ contacts when it can. If you start a chat from PC, it tends to search all of Google+ (which has never, not once, been of any use to me) and not my contacts. On the mobile side it gets that right, but still links up G+ for my contacts that have it. It's sometimes a bit confusing - did I just send them a google chat message, or a good 'ol SMS through my GV number? Kinda funny, and I know everyone hates it, but Facebook Messenger got this right.
I will also say this, if you make phone calls with these guys, keep using regular 'ol phone numbers for that. Running calls through data on the go (with any service, really)... well, that has its own whole set of issues. A bit unreliable, hopping APs/switching to cell signal, etc. Oh, and if you're on iOS instead of Android, this stuff handles even worse - on Android, the app can actually pop up when you receive a call (vs just giving you a notification, which looks funny once the call has timed out), and there's some better AP-hopping functionality in the new versions so the voip call doesn't drop. Still not enough though. I finally gave up and dropped the darn thing entirely (as nice as wifi calling and international use is on GV).