I would also recommend playing in an online league first. I've even played in several online leagues and still had troubles setting up an online league as a commissioner, but do not let that deter you! If you have a patient group, or like me, family relatives, who do not mind a few glitches or a slow start, then I say go for it.
I use
AllSimBaseball
Fidel is awesome getting you set up and has great videos and offers more tech support than I feel like I'm paying for. It is 7 dollars per month and really the best way to go unless you are very computer savvy.
PS, I'm in no way getting paid or reimbursed for that advertisement.