After about 5 hours of troubleshooting, I found out why the timed drops were not working for me.

Default Config:
"Use ServerTime": true,
"ServerTime": {
"6": "ad.massdrop 3",
"18": "ad.massdropto 0 0 5 100"

The ad.massdrop was preventing my timed drops from working. As soon as I removed the "ad." everything was working perfectly. Maybe someone can confirm this and fix the default config if it is confirmed that the issue is caused by the "ad.".

Edit: Changed Use ServerTime": false to Use ServerTime": true to reflect the config I have been using.

you have use servertime set to false in your settings above...

That was from the default config I promise I didn't miss that after all the time I spent troubleshooting haha. Thanks for pointing that out anyway