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Joe_G.Jason, I think you could very much enjoy collecting Chicago Old Judges as there are many different players & poses represented. Given your budget, you might want to consider narrowing your collecting scope to a more specific subset of Chicago cards.
For example, you could go after just the 1887 '0' numbered cards which would exclude Anson (not issued card until 1888), the 3 script cards of Kelly (King Kelly has 3 "script" poses with Chicago and 7 "short number" poses with Boston), and the somewhat difficult "short number" poses of McCormick. (note Kelly went to Boston & McCormick to NY Mets for 1887, but the early issue of the script and short numbered Old Judges show them with Chicago).
Such a focus ('0' numbered Chicagos) would take many of the expensive cards out of the picture but still leaves plenty to strive for. Who exactly is left?, well the following 12 players:
Fido Baldwin
Tom Burns
John Clarkson (HOFer)
Tom Daly (see example above, a beautiful "0433" numbered Chicago)
Del Darling
Silver Flint
Emil Geiss
Fred Pfeffer
Jimmy Ryan
Marty Sullivan
Billy Sunday (popular, but cheaper than HOFer)
Ned Williamson
You could first strive to collect one of each player then move onto poses if you wish. These 12 players were issued a total of 63 "0" numbered cards (average of just over 5 poses per player).
Pros to collecting this way include a common theme (all have the same background), are among the more plentiful Old Judges, and have an interesting Goodwin & Co. numbering scheme in nice blocks of numbers (0372-0389, 0430-0439, 0442-0465, 0470-0480 - maybe I'm strange but I think it's neat to take a set that was numbered by the manufacturer 120 years ago, distributed one a pack, and pull them back together).
Just food for thought, you could make each purchase as the money allows. You could probably complete the 12 players within 1-2 years if you accept low grade cards and maybe splurge on a Clarkson & Sunday.
Best Regards,
Joe Gonsowski