Shooting later isn't as big a deal, it just mean he might get higher numbers. Shooting earlier is more an issue, especially if he's in lower numbers. It can act like a dose increase, and if he's already at a good dose, it might mean him going low. I had a monthly meeting that meant I had to leave home close to 1 hour before shot time. I just shot earlier for a few days before hand, the just shot 1 hour later the next day. Or if in higher numbers, I'd spread it over 2 days.
Vacations - hopefully you can find someone to help. Often the local vet clinics will have a tech or other staff who is good which giving shots, and willing to stop by twice a day. I'm lucky that I have a petsitter who has given insulin shots before hand. Depending on if the petsitter will test, we might adjust him to a bit lower dose where we know he'll be safe while you are gone. Neko came on a couple trips with us - she did fine hotel camping. We've had people go on an African safari and I had a friend with a diabetic cat go to England for a month with a vet tech coming by. Start doing your research now.