Before I get to how to solve for lesser pieces, I'll assess what Theo has done since taking over regarding the 40 Man Roster. While the previous administration tied his hands over Matt Szczur, Epstein has gone 'over and above' on rendering 40 Man slots irrelevant. Gerardo Concepcion and Jorge Soler have 40 Man slots, along with Lendy Castillo. He has majoered in "40 Man Jenga", and he'll doubtless try to add a few more 'future options', be it a la Valbuena or another Rule 5 guy (collective groan noted). When Team Theo grade out a talent, tradability and upside are definite considerations.
If I were to put an over/under on how many trades the Cubs will make before September First, my line would be 4.5. Trades, not players traded. When assessing value, the bigger ticket guys (Matt Garza and Ryan Dempster) seem easier to create a trade for. While it won't happen, it's easy to spin Garza and Vitters for Castellanos and a piece than trying to figure apt value for Paul Maholm. It's not that easy determining top-end payback for a MOR guy (if moderately generous.
a bit about scouting services. Three things they respond to are youth, hype, and proximity to the bigs. So what type of player would be attractive to Theo, but might be a 'tradable asset' (not in the Top 150, or whatever). With 40 Man Jenga rules in play, youth would be nice. There are a number of guys who have been pros for over a year that few people know much about. Where, pray tell, can this list be found? It's called, the 2011 Draft Class.
These guys are still very young (professionally-speaking, at least), and have a track record. Our front office was in at least 4 draft war rooms last year (Cubs, Padres, Red Sox, and we filched a Yankee staffer), so there are plenty of opinions. They can be easily scouted the next 3 weeks for changes in form.
So, how can you chip in? Look up a team's 2011 Draft Class. Ignore the Top 2 Rounds (nobody wants to trade them yet) and focus on Rounds 3-6. Find a guy with decent numbers this season (If he's doing too good, they probably won't trade him.) at a position of need for us (SP, anybody?) and work from there. For a deep bench player (Reed Johnson?), extend the search a number of rounds. For a reliver like Shawn Camp, you be the judge. It's not like Matt Karchner ever netted a Jon Garland.
Have fun with it. These guys will usually whiff, but for Paul Maholm, you won't get a 21 year old ARod.