It's a real challenge. I love reading about the fall of the USSR. The average Russian loved us. They were ready for Coke, Levi's, and rocknroll.
Then they got oligarchs chopping of the former republic and corruption. "Capitalism is this?!?? " And with it we lost that window.
If we had brought Russia into NATO it seems hard to say if that oligarch corruption could have been stifled. Or if we'd be stuck with Russia as an oligarchy pulling allied strings for personal purposes.
Yeah man, it's impossible to say what would have happened.
As hard as the 90s were though, I feel like Russia was moving into the right direction under Yeltsin. Oligarchy was terrible then, but not the same as it is now. It actually has become worse under Putin.
All of Putin's childhood friends and college mates are now billionaires and multi millionaires. There is no independent judicial system, or media, and whatever parliament they have is ruled by one party, where worshiping Putin is a requirement.
They have to move away from executive centered government, basically cut down the powers of the president and figure out a way to establish independent courts. Else Russia will be stuck in perpetual age of corruption for years to come...and will keep dragging all their neighbors down with them.
The only thing that got better under Putin is security, arguably. But otherwise all of the old mafia has moved on to become "legitimate" businessmen and politicians.