> There was no "Marshall Plan" after the Cold War like there was after World War II. This was a huge mistake
This notion is based on ignoring historic facts. Germany (and Japan) in WWII were fully vanquished foes whose entire socio-political system was redrawn by the victors. Marshall plan executed in an environment of near total control over Germany. US simply was not in a position to do a Marshall Plan for ex-Soviet Union.
> The United States didn't do enough to help Russia transition to democracy in the 1990s.
This is another nice sounding but entirely wrongheaded thought. Do you really think an outside force can come and force a nation with its historic trajectory and 'make them democratic'? Democracy, or whatever goes by that name in the West today, has its roots in Magna Carta! That's 1215 [yes, I watched Better Call Saul]. Read up on history of England, and how much bloodshed it took to go from there to a parliamentary system, with (important to note) its entire elite class on board with the political arrangement -- it was after all what they wanted after having their Glorious Revolution.
The idea that a bunch of Americans can waltz into Moscow and St. Petersburg and turn Russia in a "democratic nation" by some means of time compression squeezing in centuries of organic development into a couple of decades is frankly laughable.