I was wondering if its possible to get all trophies in one playthrough, or at least how to get most of them. Any info on how to get them would be appreciated.
As for Matchmaker Trophy ( Zuri & Joey ), it is a one time event but the Hiking Trip is repeatable event. When both of those events triggered, however, are pure RNG.
After you got to know Zuri and Joey for the first time, go speak with Joey the next day or days later to trigger the Matchmaker event.
The Hiking Trip is available on every Wednesday. Go upstairs and, if triggered, Josef will invite you to do hiking together.
As for getting All trophies in one playthrough, it is possible and personally there is one trophy called Heroics ( Sofia Route ) that entirely depends on your preferences whether you want to get it or not.
To unlock Training Trophy, you have to start Ken Samantha Sharing Route first. Basically choose the dialogues that push both Ken and Samantha to have sex with each other. After that, go to their house the next day and, if triggered, you will find them having fun. There will be a dialogue of you asking Ken if he wants to join Samantha at the beach, but Ken said he is afraid of water. On the same day, go to the Public Pool and rent the place for $3,000 to train Ken along with Samatha. Do that for 3 days straight and you'll be able to finish the Training Event. The bonus scene is you can invite Adrian to join in the Public Pool as well.
For Future Trophy, basically just go to Mario's Villa and straight to the library. You can see that there is a button ( more like a peep hole ) on the shelf in the background. Click on that and it will open new secret area within Mario's Villa.