What your friend is asking for amounts to Initial Operating Experience. All 135 operations pair their new pilots with more experienced pilots for a certain amount of IOE, and in some parts of the country it’s with the specific intent of showing the new guy how to read the conditions and make successful approaches and departures under the varying conditions.
In the Part 91 world I think a guy could learn a lot more and potentially avoid some bad situations by having an experienced person in the plane with them. Sometimes, when you’re just starting out, you can awfully close to the edge without realizing it. With an experienced person in the plane they might be able to help the new guy recognize the situation earlier. And in these forums more experienced pilots have discuss their approach to sizing up a situation, and several times I’ve said to myself “That’s a good technique; I wouldn’t have come up with that on my own.”
I can think of a couple of times when the guy in back was WAY more experienced than I, and even when they were too polite to give me the dope slap that I deserved I still learned from them. Have your buddy keep looking - he’ll find some folks who can help.