06gsp, you've been added to the private league forum. It should show up toward the bottom on your list of SimLeague Baseball forums. I've bumped the most-recent list of keepers and last season's draft so you can get an idea what kind of players are available in the draft and what other teams keep. Basically, you want to keep your best 15 players for 1991 or earlier years, which sometimes means cutting useful players. Players without a 1991 season can be kept as injured reserve players — half their salary in 1990 (or the next season they have) counts toward your salary total, which is used to determine draft order, so you don't want to keep an IR player who is no good in coming seasons.
The biggest difference between progressives and regular theme leagues is that the pool of players is much smaller, and performance is closer to real life than in a typical theme league because it's rare for a team to have a great 1-8 batting order or 5 top SP and 3-4 closers. There are times when your team will not be competitive as you rebuild from retirements, and it's common for contending teams to trade draft picks (usually just the next season's picks canbe dealt) for players who improve their chances in the current season. Some owners try to build the best team they can each season; others look ahead and try to build a super team for a 3-5-season stretch when the players they already have will be at their peak, drafting players who aren't as good now but are strong when their current players peak. In most progressive drafts, once you get past the second or third round the players left are decent but not stars.
There are plenty of owners here who have had more success than I have in progressives, and they can probably be coaxed into sharing an opinion or two.