You just need to pay attention as to when events occur: ie - if you order the Uniform on day 11 the 3 day period for delivery would have it arrive on day 14, the same day as the Carnival... that is probably what caused the delay in your game.
Yes, but still, is a bug that must be fixed, if you can performed or not in order to reach Jack/Jill lv30 on physical strength before May 14th there must be activate another event, something like Van Hellsing discover the Gear in the Shop and seize the Witch Hunter Gear so, now alternative mission is to retrieve it without being seen or lost the event of the carnival and when it came the events related to the vampire on the cementery, after that in a few days later, the couple who live in front try to be invited into your home (so the vampire of the cemetery never shows up in your home), and now you must defend your home with Jack/Jill from them.
Or more simple, you miss the carnival and you never known who are the couple that lives in front because you now kill them as vampires in the horde that attacks Sam and Jack/Jill on the cemetery, so the developers, writers and artist doesn't need to come up with new content to fix it because you miss entirely the carnival and received the Gear late (after May 14th). Whatever the solution the developer choose to fix it, it must be fixed because it's a bug just beginning the game and the player (once the game is finished) doesn't need to know if miss something or not, the player just need to enjoy a smooth play, that's it.