I have been watching a series on OOTP Baseballs twitch archives called
The Big Rich Machine. It is a series of streams of two people taking on a Reds franchise. The first guy is at the computer and streaming and doesn't seem to have too deep of a knowledge of franchise and the guy on the stream with him has to be one of the most in depth, knowledgable people that I have ever seen in any video about OOTP.
They have literally spent around 12 hours going simply on off season stuff, which is as far as I have gotten. The knowledgeable guy literally fleeces the AI in some trades though. But he does a good job of explaining why he does things and I have learned some nice tips.
Here is the Twitch channel
https://www.twitch.tv/ootpdevelopmen...=all&sort=time