[Viva Los Expos]

It's doable, but I would recommend (1) keeping the league small, at least to start; and (2) not doing more than 2 sims a week. Entering changes manually for every team in the league can really add to your time committment as commish. I can't imagine what a headache it would be to enter changes for every team in a 30-team league.

When my league began, I was the only one with the software. (Like you, I started the league with people I know.) It's worked out because there are only 12 teams, we only sim twice a week, and as time went on most of the more active owners ended up buying the software so they could tinker on their own, and encouraged the new owners they recruited to get it, too. Now I only have one owner who doesn't have the software, though occasionally others will send me changes via email.

Good luck.