When I was a kid in the '90s, my dad and I were both progressing through the game at our own separate paces. He was always about a rating ahead of me, so if I ever got stuck, I could go to him for help.
There were a few exceptions to this, though. One of my dad's first major roadblocks was Taxing 11. I don't think he ever beat that one, because I took a look at it one day while he was at work, and beat it quite easily! I still had Tricky 7 fresh on my mind at the time, and the only significant difference was that the standard 2-blocker crowd control wasn't an option on Taxing 11. It didn't take me long to realize that a digger pit was the only way to keep the crowd from going over the edge, and once that obstacle was taken care of, the rest of the level could be beaten the same way as Tricky 7.
A few other ones we struggled with were Tricky 19, Taxing 4, Mayhem 7, and Mayhem 28. Taxing 4 was unique in that my dad and I each came up with completely different solutions. He went up the traps route it took him a number of tries before he saved enough to pass the level. I, despising traps in general, discovered the outside route, avoiding the traps altogether.