I started a 2-person keeper about 4 years ago, it's going strong with all the original members. I am starting a Dynasty League this summer. If you've played FF, then you probably know all you need to know, you just need to get organized. Both of my leagues were based on all the things I was missing in other leagues I was in (mostly redraft).
1. Pick a League Type; Establish your Rules: What type of league do you want? Spell out your rules, scoring, cost, payout; ask here in the Sharkpool for Rules for different types of leagues. Try to ask specificially for what you want...there are probably 100s of different types of league rules.
2. Collecting GMs and Money: Email and get your guys committed to being GMs. If they are not all local, setup a PayPal account to receive Credit Card payments (you can receive the payments via CC for a small fee). All you have to do is attach it to a Bank Account (I setup a little Savings Account and use that). Otherwise, just be ready to request checks mailed/cash brought BEFORE the draft if you can.
3. Pick an online provider, and see if they have enough offerings to support message board, communication, postings, and of course, scoring. I have used Yahoo (insert hoots and boos here) and they work fine for me. I just copy rosters to a spreadsheet at the end of the season, and bring them back into Yahoo come August. I little admin for me, but I have to put in the rest of the draft results anyways, so no big deal. Yahoo has a 'message board' that is 'good enough'; plus it's easy to send out league emails.
You can setup a league messageboard (for free, I think) on FootballJabber.com. If you have a website of any type, most hosts have a control panel CPanel php app that easlily lets you setup a message board. Anyways, if you want a League Message Board and don't have any ideas, ask the Sharkpool.
4. Draft day: In the past, I have just had a whiteboard/cardboard grid where people wrote in names. Last year I ordered a board+color coded stickers for like $25, which made the draft go MUCH faster. We had 8 people face to face, 2 called in on speaker phone (Saturday morning, free minutes on cell phones). I have not used software yet, but might try to project the Draft Dominator from my laptop up on the wall this year (displaying CBSSports rankings...).