SPOILER FOR BOOK OF BOBA FETT (episode 6)
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My personal head canons:
What Luke is really going to miss when Ahsoka leaves are her stories about the diplomatic general, the queen turned senator turned spy, the hero of the republic, and the adventures (messes) they got themselves in and out of. Especially the bits where his dad did something reckless (stupid) and Obi was snarky about it.
When Ahsoka leaves, Luke tries to get R2 to tell him more stories but the cheeky little droid insists on only telling him about his solo adventures during the clone wars (or claiming the restraining bolt and the thing that tried to eat him on degobah messed with his memory banks).
Every now and then Ahsoka will look at Luke’s hair or eyes, note the color, and smile.
Luke tells Ahsoka about Leía and she’s amazed how much of a mix of Padme and Anakin the twins turned out to be. She’s also not surprised that Padme’s daughter fell for a bad boy ace pilot with a devilish grin.
Luke purposely chose that place for the academy because it has enough wilderness for training - but not the kind that you have to worry about ships sinking into bogs, stepping on slime, and you can always see what’s in the water. Plus, no parent would be willing to leave their kid on degobah.