1. No. Based upon my experience (been playing OOTP since v6) and being on the forums for a long time, this would be highly unusual occurrence.
2. Yes, you can play out all of the games for your team and let OOTP handle the rest.
3. Not sure what feature to which you are referring, so I can't answer.
4. Yes, real life transactions and lineups are included for prior seasons, going back to 1901.
5. No clue. Others might have an opinion.
6. Probably depends up on who you ask. My opinion is that it's pretty good.
7&8. Since you seem to be into historical, my suggestion is to start a historical league using primarily the defaults that the game gives you. Pick a season that represents the early part of an era that interests you, and start with that. Don't worry about logos, facegen, ballparks, etc. Just go with it. Let the OOTP autoplay the games for awhile. Then jump in a play a couple of games with your favorite team. But don't stress over the details. Don't let this particular league become your main league, the one you immerse yourself in. Just treat it as a test league, and nothing more.
Do a lot of prowling around the game to see what reports are out there, how you can view and sort different things, etc., etc. Then, as you find things that you are curious about, start investigating them, search the manual, these boards, etc.
Good luck!
