Is there a way to make a chest (crate) that can be broken, grant a random weapon, and then regenerate?
Get a prop (Wooden Crate), and enable damage in the settings of the prop.
Then, get a trigger that has a delay for how long you want it to regenerate, and wire the crate to the trigger (make sure the trigger isn’t triggable by player stepping on it by going to it’s settings, all the way down to configuration stage)
The wire should be like this:
(Wooden Crate) Prop destroyed -> Trigger
Then, wire the trigger to the wooden crate.
(Trigger) Triggered... -> Make prop visible
For the random weapon, i don’t know how to make that.
I did not work for some reason
instead I suggest using a button to open the crate and run the randomizer
Try this guide.
OMG, hello fellow Stache 
Stache= the king of Gimkit