It's not difficult, it's just screwed up. Why should they have so many differing levels of the OS other than marketing and a way to make more money? You get people in with the crappy starter versions, then when they realize what a piece of crap it is, they go to the next level, always paying more to do it, and getting just slightly less crappy software all along the upgrade path until you buy the top of the line crap that's less crappy, but still crap, but you *feel* better about it because you paid more.
Bait and Switch is illegal, but this is a similar marketing method. Bait and switch is getting them in with a low-cost item, then getting them to buy the higher priced one. With the Windoze marketing, they don't switch, they just get you to buy an upgrade. Same basic strategy. Different, but unfortunately legal, method of execution.
It's also an appeal to customer vanity, jut like fashion. What makes a pair of faded, beat-up, torn jeans from a trendy shop more valuable than a pair of jeans from a thrift shop? The price is higher because of the designer label. "My jeans are better than yours because I paid more!"
Same thing for versions of Windoze. "I've got the Uber-Premium, Ultimate, Kick-Ass, Expensive version of Windows on *MY* machine! What's on yours?"
Consumer stupidity and corporate greed are what have put our society in the crapper. If you don't think I'm talking about you, you're probably wrong.