@Skylar ***********
Did you read
@T**
's comment carefully?
Your re-entry permit expires at the same time as your current stamp, NOT your work permit.
Anytime you leave Thailand you need a re-entry permit, otherwise, you lose your current stamp (entry, first 90days or extension) and you have to do the process over again. Depending on your stamp, you can decide which of single or multiple re-entry would be better.