As one who has more than once confessed on this forum to a pesky libertarian streak, I don't identify Putin's policies with libertarianism, but there is a certain anti-progressive flavor to him. Rather, I see Putin as a throwback to the age of the Czars, behaving as they have done for millennia, ever seeking to extend Muscovy's borders and inflicted with a dose of paranoia against the rest of the world. Add to that the moral compass of Ivan the Terrible or, if you prefer, Beria and the man is fairly well explained.
Putin is not a libertarian, he is a throwback tyrant. His opposition to "liberalism" arises because he instinctively sees liberalism as a threat to his autocratic position and as a road to national weakness.
That does not mean that he cannot be dealt with or that he will not participate in deals. It is vital that the American longtime national security objective of preventing Germany, Russia and China from uniting against the rest of the world continue to be pressed. We already see that Putin will play America off by cozying up to China and Germany. Angela Merkel is all too eager to slip between the sheets with Russia. Additionally, Russia has entirely too many tentacles into the Middle East which fit neatly with its central geographical position.
A waning economy dependent too much on minerals and petroleum, Russia nevertheless remains an important player and Trump is right to see the broad geopolitical interests of the United States and he is right, therefore, to romance Putin.
I very much appreciate your thoughtful analisys but it lacks insight into a nature of Russian political processes and related discussions. Putin is actually in a long time dispute with the left and he sounds pretty much libertarian while at it.
Russia for example pursues a very conservative fiscal policy and his reforms from the very start were about to reduce big government. There was legal reform which brought courts to pretty much Western standards and he also was behind a 13% flat income tax.
That oil economy is not really true as well. The share of mineral extraction in total Russian economy is just marginally above that of US. It is true that the energy business was historically taxed excessively in Russia which made it the biggest contributor to the federal budget. It is actually changing now.