The "Old Boys' Club" issue with the Oilers pretty much ended about 4-5 (?) years ago, so I don't think that's really an issue anymore. They've long since gotten over that hump. The key moment was the severing of Kevin Lowe's degree of power over the team. (He's effectively retired now.)
Some ex-Oilers have had excellent results with the club. Lowe himself was the GM when they nearly won the Cup in 2006, but thereafter he was hobbled by his enormous ego (see: Battles with Brian Burke; the press conference from hell) and his crony-hires (see: ex-Canuck Steve Tambellini, the most baffling and pointless GM hire in Oilers' history).
Craig Simpson's (1987-1993 Oiler) brief tenure as an assistant coach was well received, and of course Charlie Huddy for several of the past dozen years was one of the more respected assistant coaches around the League (notably in Winnipeg, which had considerable success when he was around). He was one the Oilers' let get away just when they could have used him.
Craig MacTavish (latter-half dynasty player; also on great clubs in Boston and New York) was arguably the 2nd greatest coach in Oilers' history (he or John Muckler). He was hired as GM by Lowe and lasted about 15 minutes in the position. During this time, he managed to draft Draisaitl (major win) and hire Dallas Eakins (epic fail), the latter of which sealed his doom. But MacTavish is a great hockey mind and I think he probably would have had success as a GM if he hadn't hired Eakins. That was the hire from hell.
Anyway, the "Old Boys' Club" country-club atmosphere seemed to end, as I said, about 4-5 years ago and not a moment too soon. The one complete dead-weight fossil whose existence still tries the patience of the faithful fan is not an ex-dynasty Oiler but rather Bob Nicholson. I have yet to figure out what he does and he's been on the job for six years. He makes horrible speeches sometimes, to the media, at the end of seasons.
Paul Coffey, I think, is a different animal from the Gretzky-Lowe type who drinks the wine and toes the company line. Coffey has always been an outside-the-box personality who doesn't shy away from saying what he thinks, something the Oilers need more of. I was a little concerned when they hired him as a PP-consultant a few years ago (shades of "old boy syndrome" yet again), but he kept a very low profile and, after all, their PP suddenly became historically great, so no complaints! I suspect that Coffey himself is well aware of the suspicion certain fans have over his presence, so he doesn't want a title or to be a visible part of the management group (which he isn't).