Please understand, I didn't mean to lecture you or sound parochial. For me it comes down to three things:
1 - What boundaries did you set for Him and where do his actions fall within that circumscribed pretext?
2 - ROI: What do you ultimately stand to gain (tangible and intangible) by continuing the friendship vs the assessed financial and intrinsic worth of that tangible object?
3 - With you being His senior and his past mentor-ship being very possibly lackadaisical, what could you both stand to gain by putting your experience to work, by teaching Him, while He's teaching you?
I ask because that's literally the definition of my daily job now, (plus about 5.8 trillion other semantic and pedantic details); to put my knowledge, experience and wisdom gained from my 19 years in the A.F, as a Senior NCO, to work in the mentoring of those who will replace me, and hopefully do a much better job than I have. I have always been a fairly straightforward and upright person (recently described by a friend as righteous, though I hadn't thought about it from that angle) and have long maintained that what's good for the Goose is indeed good for the Gander. And, there are times that I've let my temper get the better of me when I was pissed, (even though the anger was well-founded and justified in my mind), but it took losing out on some potential opportunities because I was too' concerned about being right or fair, to see the larger picture, (under the axiom of win the battle to lose the war).
The older I get, the more I grasp just how astutely observant (and right) my (Late) Great-Grandmother Kent was, with many of Her sayings, Her favorite being: "You catch more flies with honey than you do with vinegar." I do miss that lady greatly and wish I could thank Her now for all of the pearls of wisdom that She granted me, while I was far too young, infantile and immature to understand them, but I know that in Her quiet, unassuming way, that She was planting seeds and hoping that they'd grow with at least one of Her Great-Grand Children, and they did.
I apologize for the novel, but thought I ought to clarify my reply, lest the wrong tone be received. Take care, and I hope it works out well for you regardless of the path you choose.