I don't think we'd have had any staying power in Russia during the revolution, but a Russian writer did speculate that if the Crimean peninsula south of Ukraine had been an island, a free Russian "Taiwan" could have developed under the protection of the British fleet.
As to the bonus question, I wasn't thinking so much of Lincoln, though it does fit and raise interesting possiblities.
Hayek and others who lived through both world wars attacked Germany, even the Germany of 1914, for being the statist and repressive power. Today, Taki, Paul Gottfried and others think a victory for Wilhelm's Germany would have been a victory for freedom.
Maybe, given all we know about what happened after imperial Germany didn't win ... but ideas of free speech, representative government, and above all free trade were closely tied to Britain. Had Germany won, managed trade of the sort that developed in the thirties would likely have become the rule. And this would have really agitated some who speculate on the question. It would also have been a victory for Hegel over John Stuart Mill, and for repression and vote manipulation over a more disinterested attitude of "fair play" for all.
I can admire these Rockwell types for asking interesting questions, but the answers simply seem to be, "whatever happened was wrong." The reasoning seems to be A) This side won a war, B) The powers of the state grew after the war and personal liberties shrank, C) Therefore if the other side won the war, the powers of the state would not have grown and individual liberties would not have been curtailed or reduced. The other alternatives are that things would have been much the same, or that more freedom would have been lost. As with the American Civil War, the Rockwellites don't see that the losing side may have had its own imperialism, militarism and statism.
In 1914 Germany was the rising power looking to change European affairs. They were more than willing to apply in Western Europe lessons learned and repressive tactics used in the colonies and in Eastern Europe. They favored extending and expanding the statist and managerial ideas that they had already developed and applied at home. The Germans of 1914 were not above using relativistic, might makes right arguments to justify their actions. England and France had also advanced along the same path, but nowhere near as far as Germany did. Under the influence of war they continued on that road, but once again, Germany went further.
Had there been no war, we probably wouldn't have seen the very ugliest side of statism, and anything that would have prevented the rise of Hitler and Stalin would have been a good thing. But that doesn't mean that every possible German victory would have been superior to every conceivable alternative.
In regard to TR: Without Lenin or Stalin, socialism wouldn't have been discredited as much as it was. And TR was ready to go some distance on a socialist road had he won. But under our system it takes some crisis or breakthrough for a President to overcome congressional opposition to his plans. In the long run, the war and all its consequences went a long way to making socialism less attractive. In the short run, though, Wilson, like other political leaders used the war to get more statist or socialistic measures through, some temporary, some more permanent.
It was thought by many at the time, and I don't know for sure that he did, that Wilson and certain English liberals sympathized with the Russian revolution. The reason people might have thought it good is because they applied the groundless principle of power to the people, blah, blah, blah. Europe of 1913 was awash in this.
I'm not thinking that Roosevelt was headed towards socialism, per se, all the to each to his own, etc. I erred above in saying he'd have gone beyond the New Deal to socialism. He was too shrewd for that foolishness and it grated at his conception of self-reliance. He stood for min. wages/ max. hours, etc., and not just to the railroads, but all businesses, which is a given today (outside of LewRockwell.com...). The danger lied elsehwere.
What bothers me about him, the New Nationalism speech especially, was this deliverance to big business as an unavoidable fact of life. He was headed towards, as I said above, a government-business partnership, which is the far worser aspect of socialism, or national socialism, or communism, than New Deal social programs. If this means anything to you, check out what George Perkins was saying about the relationship between business and government. I'd be happy to post or send you a copy of an interview with him on the subject from 1912. This was "managed trade" at its worst, the German impulse you describe above.
Roosevelt's belief in the triumph of business was almost Marxist in its historical assumption. Here is why this thread moves me in this direction (and I hate to keep bringing up TR): Fukuyama makes the same mistake with his static view of history (correct me if I am wrong).
Your explanation of 1914 Germany is on, especially #19.