re: Fantasy football keepers with assigned values...

We use pretty much the same keeper system in my league.

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1. If a player was picked up as a FA last year and is tabbed as a keeper this year, what round value should be assigned to that player?

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We count FA keepers as a last round pick.

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2. We do keepers for a max of two seasons, so if a player is kept this year at a 5th round value, and the same player is then again kept next season, does he still hold the same value of 5th round? Some in my league think that because you've optioned the second year for that keeper, then he should have a round one value for the second season?

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Our keepers move up 2 rounds per year. So you draft a guy in the 7th round. Want to keep him next year he gets a 5th round value. Keep him again and he gets a 3rd round value. Keepers for a max of 2 seasons.