Going to be honest. It has been handled by people at the store because one can see a very faint line where the flap would open. Most boutique-fresh/mostly non-handled bags do not have this. Only you would be able to determine if it's worth the ~$1k USD in savings you get by having your BF buy in HK.
Other than that, no major issues from the photos you've provided. If I were making the decision, then yeah I'd relax and enjoy the $1k in savings. There ARE bags I've seen that are obviously crooked, or have blatantly poor stitching, very poor leather batch, etc. and on this one nothing very bad stands out.
Your list is very long, even as a Chanel lover and who enjoys shopping there with/and sharing with friends...I don't think I'd have the patience if a friend asked me to go over the checklist of details in purchasing for her.
I am VERY careful about sharing my luxury enthusiasm with anyone. My parents/extended family are very nosy and none of my past BFs were enthusiastic; I don't even feel perfectly comfortable with them looking at me browsing on my computer. Even if they see me being very financially literate and responsible, I run in circles where it's like "but you can do even better..."

Try to contain your enthusiasm if it's not shared too much by others, and be as tactful and graceful as possible when making any requests for them to check for stock.