IMessage Overseas Logistics

My boyfriend is going to Shanghai for work for a month, and we are trying to straighten out how iMessages between our iPhones (him=5, me=4S) will work best -- neither of us have tested this outside the US so I'm hoping for someone with the same kind of experience to tell me if I have this straight:
He's planning to turn Airplane Mode plus WiFi on, since Verizon apparently doesn't deal well with Chinese coverage (according to his co-workers who have already been there, although I find that hard to believe in "TechCentral" Shanghai) so he isn't planning on buying an international package as he'll be busy teaching in a plant all day anyway.
His hotel is supposed to have good wifi. We tested iMessage and FaceTime here in the States already with him in Airplane mode and on wifi, while I was on wifi, and of course it worked just fine like it was supposed to, so we should be able to be in touch when I'm at home and he's in the hotel.
Here's where I start having questions: 
1. If, here in the States, I message him and he's not around wifi while he's at work, will it give me a "not sent" error message, or will it wait to go through until he's back in the hotel on wifi?
2. Conversely, if he sends me an iMessage and I'm out and about, will it actually send to me even if I'M not also on wifi?
          Obviously I have a data plan (AT&T) and messaging, I'm just wondering if one iMessage is sent out over wifi with Airplane mode enabled, does it absolutely require the other party to also be on wifi? Clearly iMessages send all the time here in the States using data plans while away from wifi, but I'm interested in what it does if the sending party has NO cellular data enabled while the receiving party does.
        I think I'm overthinking this and it doesn't matter which party is on wifi and which is on celldata as long as both parties have SOME kind of continuous data-transmitting connection, but am hoping for confirmation from someone who's been through this.
Also if you have any international travellers' iPhone tips or pitfalls to share, it would be much appreciated.

1. You'll probably get the Not sent message.
2. You don't have to be on WiFi. Cellular data will work just as well.
Your boyfriend's Verizon iPhone 5 is a completely unlocked phone. He has the option of getting a local SIM. He may be able to find something that gives him a better deal on data.

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