We went through expansion twice in my online league. I won't detail the whole process (unless you would like me to) but here are some key things I thought of off the top of my head:
- The #1 most important thing is finding active owners for the expansion teams. This will greatly help in keeping the expansion draft moving quickly. Maybe even float the opportunity to current owners and try to find a replacement for the existing teams instead.
- The best time to expand (IMO) is right after players file for free agency but before any free agent offers are imported. This prevents teams from making the mistake of protecting players who are heading to FA anyways. It also gives the expansion teams the chance to fully participate in Free Agency and the Rule 5 draft. If you hold your amateur draft during the off-season you should probably allow the expansion teams to participate as well.
Other things we did that I liked:
- Only expanded by 2 teams at a time. Expanding by 4 in one season is too much IMO. The pool of available players is too small and existing teams lose too many players off their 40 man roster.
- Gave the expansion teams the #1 and #2 picks in the draft their first season.
- Turned off scouts for the expansion teams while drafting. It's hard enough to build an expansion team without having to deal with scout randomness.
- Automatically protecting the last two amateur drafts without teams having to use one of their slots.
Things I would do differently:
- We limited the losses of a single organization to 2 players per round (5 total). I probably would raise this limit slightly.
- Setting expansion teams to the lowest market size. I'd probably put them in the middle or assign them randomly.