I did two attempts this past month on my twitch channel that have ended in game crashes over 5 hours in. After those two heartbreaks, I decided it's not worth it.
Also you cannot just save and load the game when it crashes, as that would basically make it a segmented run, so a game crash = instantly dead run.
Recently I made a route for bully classic 100% and submitted a speedrun which followed said route. (Well 85% of the run followed the route as I had to make a couple of imrpov adjustments due to failing a couple of missions etc). The route can be seen here: https://docs.google.com/document/d/1tN3XpBDJgejkwsghnoisXZkDz4SLzIwpGGULPfdHdUc/edit#heading=h.v2ff6dyven2p
As with all the routes I've made - I won't say its the most optimal route that could be possible for the game: I haven't timed every possible route alternative - there are many 'divergent' pathways in a 100% run. But there are definitely time-saves in it and everything that needs to completed to reach 100% has been listed (and when to complete them has been noted).
There are two things of note that should be mentioned. Firstly, once chapter 5 starts I don't start the mission Making a Mark until Gym Class 5 is completed (which gets completed on the third day of chapter 5). The reason behind this by commencing Making a Mark the gym building becomes unavailable as its get burnt down. I wasn't too sure if the gym building becomes available (to do gym classes in) after completing Gym is Burning or not; so I just played it 'safe'.
And secondly, in the route I note how to obtain enough money to be able to purchase all clothing (at clothes store) before the credits (normally you can only purchase all the clothes after the credits once you've gained $300 by unlocking all yearbook photos and extra money). This was only possible by earning $400 during the mission 'Tagging' (thanks to TheNathanNS for this!) and earning an additional $500 off midget wrestling during Photography 5 class (with the help of a plank). This strat didn't go well in my first run since I screwed up a couple of bets and had to ditch the idea since I wasted a lot of time trying to earn the extra money. But, it should be possible to win 5 bets quickly with good RNG.
