You mentioned bullying Yuusaku to pass time AFTER trying to get the Weekend 3 event, but I would say the key time to bully him would be BEFORE the Weekend 2 event (i.e., BEFORE the dentist visit). Bullying Yuusaku gives romance points that you need to progress through the events successfully, so if you have already progressed to the Weekend 3 event, then bullying him afterward won't really help.
Regarding the time, if the clock says it is 5 PM, and then you go to Ogata's apartment for the event, make sure that it is Weekend 3. You cannot complete both events in the same weekend (e.g., if you do the dentist event and then try to do the dinner event during the same day, it won't work). You have to progress to the next weekend in order for him to be in his apartment to meet. One other thing you could try would be to go to your apartment and just spend time until it is 6 or 7 PM and see if anything changes, but it should work to go to his door at 5 PM as long as it is Weekend 3. If you are still running into problems, comment again, and I can do a more thorough code examination, but I prommy lots of folks have gotten through Ogata's route, so it should function as long as you follow the hint sheet. Apologies for the trouble it's causing you... :'(