Thanks for the feedback. Just ran a quick simulation of a snake draft using H2H points values on first year leagues and found that for 32 players per team (leaving 8 spots open for FAs), you get an average team value of $364. The first two teams have higher because of Trout/Betts having such high values ($385 for the Trout team and $375 for the Betts team) and then all other teams are between $357 and $363. I would assume leaving 8 free agent slots at around ~$36 of cap room is fine but let me know if you disagree. As for distributing players by position to get a roughly even distribution, that looks tricky, but if one team is overloaded at a position it would just encourage trading. Anyway, I think it could work.