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I agree with BlueNoser: start a fictional league (local, global, national all up to you) and start playing. the options are numerous but pretty self-explanatory. the most fun I have in OOTP is draping narratives to fit the incredible stats and simulations it generates and this is much easier and more fun in fictional leagues. once you play around for a year or two you will get a good feel for whether you want to manage each game batter by batter or playing as GM or maybe just playing as commissioner and watching and "covering" the league like a journalist before jumping in and taking over a struggling franchise. I love playing massive worlds where there are hundreds of teams and lots of different leagues all across the globe and then taking control of one team in a small part of the world but some people like playing 8 team leagues in England. part of the fun is finding out which way suits you the best.
the important differences in gameplay mechanics are the accuracy of your scouts (if you play with scouting on) and what the AI evaluates players by. search the archives for threads talking about pro and con of these approaches. as far as user interface goes, there are tons of great logo sets you can find here or on OOTPmods.com. having the real MLB logos if you play with real players or having some sort of created logo (not the defaults) if you play fictional is a small thing with huge results. it makes the game feel much more real if you add logos
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