I don't have a ton of experience with the fictional leagues, I have done just a couple but also in the process of setting up a more in-depth world myself.
1. I have tried both, it really depends on what you prefer. I am currently starting in 1900 and going to sim until at least 1950, just to get some history, records, etc. on file. All fictional players and teams, so I will name my "Cy Young" award to another pitcher, possibly name the MVP after a hitter as well.
2. This is my biggest question still...any help on this one I would greatly appreciate as well.
3. These are all options you can turn off if you don't want them to happen while you are simming multiple years. I turn off everything except for more/less pitching and more/less hitting. I spent way too long compiling team cities, names, logos and hats for somebody to relocate or add another team on me.