I unequiped my own gamepass from my inventory to try out purchasing. However when buying them in studio the local script works fine but the server side rewards dont work.
My dev products work as well its JUST my passes. I want to test if buying them in studio is just the issue or not. And since i cant buy any of them due to my robux amount being 0 My only hope is to reeqip my OWN passes.
Yeah, you didn’t unequip it. You deleted it from your inventory.
Only thing I can suggest is either setting the price to be R$1 briefly, allowing you to buy it for as cheaply as possible, OR you can create a new gamepass in place of the actual one
(edit: You could also modify your code to assume the player always has the gamepass - if PLAYER HAS GAMEPASS or TRUE then)
still to poor 
Huh? Aren’t gamepasses free in studio? Why would the issue only be in studio?
What I would recommend is making a role system, in one of my previous projects we had created a full role based system that basically managed everyone’s permissions on what they had access to, for reference it was a border game so we had it managing what Teams a user had access to Join, Tools a player had access to, Gamepasses a player had access to, Even vehicles groups they could spawn.
What this allowed us to do was if we wanted to gift players free gamepasses or give them a particular role we could just add it to their data.
I had also used a similar role structure for a prison game I worked on previously and in that we managed Tools player can get from the givers, doors the player had access to, teams, etc.
Within these roles we basically had permissions they had in the script it would just verify if they had that role/permission but we also had role requirements basically things they would need to get access to that role. So in that we had stuff like if it was enabled on their datasave, if they owned a particular gamepass, if they were in a group or a role of a group, duration played in the game, admin levels & stuff like that.
But basically like the other guys stated you can’t repurchase a gamepass if you owned it previously and had deleted it from your inventory though it would be smart to implement a system so you don’t need to purchase it at all and could just give it to yourself for free without having to pay for it.