Okay - its time to answer my own question lol, after scouring the depths of each of the forums, patreon(which btw is worth the sub) and the available guide I have pieced together all the information I could find and test myself. So I'm going to leave this info here for anyone who is looking for the answer as well since the patreon guide doesn't have any info on quest 54 and the other guide available doesn't give any dates or other requirements necessary and I will do my best to give this info without giving any of the spoilers.
Quest 54 unlocked pretty consistently in first week of January right after finishing the main story content and getting into the sandbox mode. Create a save before doing the flying lessons on the first Friday. From there do the lessons as usual if you don't get sent to the hospital overnight you can just reload and try again until you end up there overnight which is how to unlock that quest and its fairly linear and quick.
As for quest 74 after spending way longer than I care to admit passing each day away the quest unlocked in November (according to the guide it may also trigger in December) only in sandbox mode. Obviously that takes a lot of time playing each day from January 1st all the way to November 1st. So for anyone who wants to skip right to the start of that quest if you press Shift+O (the letter not number) to open the console (sorry android players I have no clue if console is available on your format) and type ''theday = 31'' make sure not to include the quotation marks, it will automatically skip you to the end of that month. If the month doesn't have 31 days then it automatically skips to the next month so don't worry (this speeds the process up substantially if you solely want to play the TF content) As soon as you reach November just go into the hospital wing and *voila* quest 74 should start. From there the rest of the quest should be pretty easy to follow.
The quest may potentially be able to trigger during a playthrough if you are maybe extremely lucky but I have not ever had it happen to me so I'm under the assumption its sandbox only. However it would be cool if it can happen during a playthrough right before the end of the story. (If it does I will update this in the future)