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Watching baseball is probably crucial...there is usually some good information to get from either commentary during the game, or pre/post game footage.
You may also want to start small. Take in charge only a few elements while leaving the rest to your assistant. Then when they make certain decisions, you can look for why it makes sense.
Something underrated as well is you may want to start a small fictional league with only a handful of teams just to get situated, and use that as your "practice" league. The MLB startup can be daunting (especially if you add all the international leagues) so sometimes a small league with like 8 teams total is perfect to start learning.
Something else you could try would be to start 2 identical leagues, but take over different aspects in both leagues and compare progress made/understanding. Sometimes comparing 2 known entities together helps with putting the pieces together for some people.
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