I was informed recently by Those Who Know that alternate history is either "dead" or "rubbish" because there are too many factors in the major events - the prime example being that old standby of Germany winning World War 2.
Now, while I agree that the end-point of a war is something that's far too complex to be treated as a single alternative, I utterly disagree that this condemns all alternate history. Most of history is a kind of juggernaut of inevitable where the pressures of the era would produce if not the same result, then one close enough to make no difference. If Hitler had never been born or had remained a minor artist, someone else would have risen to fill the gap.
There are, however, pinch points where history can, with a bit of a push, head down the other leg of Pratchett's Trousers of Time. This is where alternate history is valid and can produce some very interesting results. Usually the pinch points are individual actions: assassinations successful or failed, edge-of-the-knife decisions, and the like. Sometimes they're circumstances: suppose Catherine of Aragon's sole surviving child had been a boy? English history would have been quite different. Or a more recent example: the Midway sea battle. The weather was appalling, and every account I've read suggests that it was pure good luck that American pilots saw the Japanese aircraft carriers before they'd deployed their planes and soon enough to destroy a hefty chunk of the Japanese naval power of the time. That battle is generally regarded as the turning point of the war in the Pacific - suppose it had ended differently?
Obviously I have a less-than-impartial interest in this, since Naked Reader is publishing my first novel, Impaler - which just happens to be alternate history. The companion novella, Born in Blood, is closer to straight historical novel, and available from Amazon and Smashwords as well as the Naked Reader site.
Both of them deal with one of the relatively few people who formed a historical pinch point: Prince Dracula, aka Vlad the Impaler. To start with, it's rather unusual that someone from a tiny buffer state between two much larger empires should be a central figure in an extraordinarily fraught period of history. Then there's the interesting point that despite Vlad's much-reported faults a change in his favor has the potential to significantly improve the outcomes. Specifically, Vlad recognized that no treaties would stop the Ottoman Empire's expansion - and predicted the fall of Hungary if the Ottomans weren't stopped by the one thing they did recognize: overwhelming force. He was, as it happened, correct.
I describe Impaler with the over-simplified "What if Prince Dracula had won?", when the real event that switched the Trousers of Time around is Vlad surviving the assassination attempt in December, 1476. I'm taking the view that his twelve years as effectively a political prisoner of the Hungarian King served to temper him and he emerged somewhat more in control of what was by all accounts a fearsome temper, as well as realizing that he lacked the resources to completely break the boyar class. That along with the realization that the Ottoman Sultan, Mehmed II (Mehmed the Conquerer) will not allow him to keep his throne drives the story.
The fun part was in the cascade of events: I dug all over the internet for obscure information about the first few months of 1477 - little things as much as big ones. Where I couldn't find any documents, I chose what seemed to me the most likely possibility given what I could find about what followed. If I get to write sequels, the impact of Vlad's survival will get wider, until ultimately his world and ours are very different indeed.
That's my road not taken. What road would you like to investigate, and why?