Sorry for the late reply, I've got busy lately.
Without further ado, here we go!
I think I see the problem. You might be overwriting the webstorage value with the last Money value instead of adding to it.
Try the following.
On start of Layout : Set Money to int(WebStorage.LocalValue("TotalMoney"))
On winning the game : -Add 250 to Money
-Set Local Key "TotalMoney" to Money
It's time for me to return the favor :)