I think most iPhone versus Android conversations have to end with we'll just agree to disagree. My experience was OG Droid, and Bionic, and my wife's Droid RAZR MAXX. We both upgraded this last September to iPhone 5s. So that's at most 2012 to 2013?
Not sure what OG Droid is to look up, Bionic is 2011 and RAZR Maxx was barely 2012 (Jan 26, 2012). Still pretty dated. And no version history to quote what version of Android you were talking about. (4.1.2 is pretty close to the 4.2 I'm familiar with from the GNex which itself is dated and doesn't suffer from your issues...)
I should clarify, video between iPhone and Android works as long as the video is only 6-7 seconds. Any longer, and it won't work.
34 second video of the niece is on my default IM on my M8 right now, recorded on a iPhone and it plays 100% fine. Same one booting my old GNex runs on it as well although with a few bits of choppiness that look similar to "buffering for Netflix" or something - but the entire video ran.
This problem doesn't exist on either reasonably recent Android phone that I have at my immediate disposal.
Oh wait, got the wife's Nexus S too - and... it runs perfectly, no choppiness even - and full 34 seconds.
And messaging, don't know what to tell you. We've sat in the same exact room, to try and get messaging to work through Handcent, or default messaging app, and no matter what we did, couldn't get it to just combine the Androids response into the group message. Maybe it's just a limitation. Android replies, and all other people get it as a single text from that user. iPhone replies, and it comes into the group "thread".
Oh you were talking about character limit then said "grouped texts" I thought you were still referring to multiple texts from going over 180 characters as "grouped texts" - not familiar with sending mass texts to multiple people at once, always 1 on 1 mine - I do know there's options to send group texts under Android however, since I have seen the father-in-law mistakenly mass text a ton of people by mistake at times. Likely it just doesn't import it by default - I can't think of many circumstances where I'd ever send out a mass text and want the responses to go to everyone, if I was going to do something like that I'd just use a different format like Facebook or email. I can't imagine "Vaclav texts - Party at my place 6pm RSVP" with everyone RSVP'ing to everyone else of the dozens I invited rather than just me, so much noise to signal.
Maybe there's some narrow applications where it's handy (and I'm sure there's an app that does similar threading) but it seems a very narrow thing to worry with. If it's even a thing, since as stated it's not a functionality that has had any purpose to me.
For as limited of use that I use my iPhone, I could probably be very happy with a new Android phone. I'm not doing anything that's required to have an iPhone, but with so many others I interact with being on iPhone, the conveniences have been nice.
iPhone does obviously tend to play best with itself. This is true.