I can see both sides.
When you're an aspiring football coach who hasn't ever been a player, you're gonna lack contacts and probably going to go wherever there are clubs that will take you. His first assistant job out of coaching kindergarten was at Shinnik Yaroslavl in Russia, under a Russian manager. Nice city, but must have been a culture shock for him, probably why he did so well in Azerbaijan. Then he was in Greece and Denmark, so yeah he's been around, but he'll have built up some decent contacts and learned a lot.
Incidentally, while he was at Neftci in Azerrbaijan, he was the assistant when they qualified for the Europa League group stage where they drew with Partizan Belgrade twice and held Inter Milan to a goalless draw at the San Siro. They are, however, owned by the state oil company and are therefore the richest club in that league by quite some distance.
But, as to your point, I guess being a manager isn't the same as just being an assistant where there's less pressure and culpability. I mean how often do you see clubs sacking their assistant or coaching staff but not the manager? Once in a blue moon at best. So him only managing for half a season at Southampton (where he did beat Chelsea away and draw 4-4 with Liverpool using a demoralised and ****ty Southampton side) and holding Reading together at the seams isn't the best resume. But like Rosie, he's gotta start somewhere and it might as well be here.
If we go down, we've got Millar and Belloumi at least. Be fun watching them tear the likes of Burton Albion and Exeter a new arsehole.