When we were on MDI with our young son, we were instructed to bolus after because you could not reliably know what he would eat. Our clinic is big on not starting food battles (i think cuz it can lead to more mental health problems later: anorexia, diabulemia, etc.) But they did encourage that we try to get him to eat in a half hour. That made me laugh because my son can be a pokey eater, so it would have been a food battle to take away his plate that soon. So we just waited even if getting the shot was 1 hour after he first started eating. So for us, the pump has been quite helpful as we can give a bolus for what we know he will eat and then just give extra boluses as needed as he requests extra food. If you son is comfortable with 2 shots, he can do that, othewise, I probably wouldn't fight it right now. Use the endo to your advantage as others have suggested, maybe call/email ahead that you have this concern and have the endo ask your son the question "When are you bolusing?" if the endo is concerned. (Less accusatory than you sitting there going, "You know, Dr. He is bolusing after he eats, isn't that really bad?" If I was in his shoes, I'd be shooting daggers at you and be really pissed and it wouldn't matter what the dr. then said.
I do respect your son's choice not to pump right now. But I also agree, that maybe it would be good to at least have him try it. I think you might get up to 90 days to try it out and still send back if he doesn't like it. Might be something to discuss with him and see if he'd compromise. I do think the actual logistics are much easier to handle than what you anticipate them to be before you actually are pumping. (I was so worried about my son sleeping and getting caught on things, etc. and these really have not been a problem.) So a test run might convince him that the freedom a pump affords is really worth much more than the downsides of 'being connected 24/7'. (And having your insulin attached to you beats having to remember to CARRY it with you everywhere, IMO.)
Good luck, Angie. You are a great D-momma.