Glad to know there's so much interest in this story type. Per the responses, I'll clarify a few things.
First, this would be a do-over based on my senior year of high school onward, not a history do-over. Sorry I was unclear on that. Lots of band and music experiences to write about. Second, historical accuracy seems to be a sticking point with most of y'all. Thankfully, my hero won't be out to change the world or anything grand like that. I plan for the story to be very personal, probably a bit darker than some of my others. It'll still have my traditional happy ending, but the road to get there will be rough.
One thing I plan to include is knowledge of sports to make it big and fund the career in music our hero always wanted. Several of you made a great point that remembering numerous horse races without Biff Tannens sports almanac is unrealistic, and I agree. My thought is to have him win big on a few football games with massive upsets from the 2007 season, like App St over Michigan and Stanford over USC. Feel free to weigh in on the plausibility of that plan.
Finally, a few of you mentioned the means of the time jump. My plan is an alternate reality to start where I had married one of my previous girlfriends that in hindsight would've crushed me. His life falls apart and just as he starts considering suicide, he falls asleep and wakes up before senior year. However, I don't plan to explain further than that. Is it God? Aliens? The Matrix? Not the point of the story. Again, I'd love your thoughts on this concept. Thanks!
M. H. Barton (auguy86)