No where close as aggressive. Windows 98 never interrupted your boot a few days after install "to complete the setup experience" asking you to subscribe to MSN or order a copy of Office 97.
The aggressivity isn't the topic of discussion, the topic of discussion is what Steve Jobs would have thought about ads in an OS, but we already know what he thought about Microsoft ("no taste" anecdote) and MS were already pushing things in Windows prior to Jobs' passing, ergo he almost certainly would have found it tasteless.
If the goal of a tool is to provide an efficient means to tackling a task, Windows is becoming further and further removed from its ability to effectively do that with layers of cruft, up-sell and dark patterns. It's not been great since the '90s.
With that said, I'm sure Jobs would find plenty to dislike in modern macOS and iOS too with all the crap bolted on top of them. Apple TV UI is a good example too. I'm sure he would have had some strong opinions on the Apple Pencil as well.
