You have to enter Thailand again within the validity of BOTH of your current stamp and Re-entry permit. You cannot enter again on your supposed-to-be-remaining stamp if the re-entry permit has expired.
Or you cannot enter Thailand on a seems-to-be valid re-entry permit if your stamp is expired.
You need to be back in Thailand within the validity of your current stamp on which you have a re-entry permit, or your stamp is no longer valid for you to enter on that.
A re-entry permit does not add any days to your stamp, it just keeps the stamp "alive" when you are out of Thailand.
When you enter Thailand on a re-entry permit you will be stamped until the exact same date on your valid stamp, even if it's just one day.
, if you want to leave Thailand through a land border after you meet your friend, don't try to get 7-days-to-leave stamp. Better go border-bounce before your friend comes.
Unless I'm mistaken, you have to cancel your WP and current extension (unless you are still on the very first 90 days from the Non-B visa), and then leave Thailand once to be able to apply for a new Non-ED visa.
No downside to ask your uni if you can do it inside Thailand. Anyway, you need to talk with your university about details of your procedure well and follow their instruction.
You can, as the Chiang Mai office accepts extension applications when you have 45 days or less remaining with your stamp.
I don't know what documents you mean by "greenish pdf". Attached is the "general" information on tourism extension, and it's not a PDF file. CM might require differently.