The Cubs were pretty good until 1945 and then they sucked up until the 80s. Before the Tribune decided to crank up the value of the franchise artificially with massively backloaded contracts, Chicago was pretty much a small market team. There's plenty of historical data on why the Cubs fail and it has less to do with their market size than you think.
Joe Posnanski
If you have some of the smartest people in baseball (arguably) and they don't think spending out the ass is going to work out this year, then I guess you can still disagree with them, but you should at least figure out why it is that they don't think spending is the right way.
I guess if you really want to make an argument that spending big is the answer, take a look at the free agent list again and ask yourself who you would spend on and how much those expenditures would actually help the team now and 5 years down the line. It'd be great if they could have pulled in Fielder or Pujols, but you do have to be a bit more realistic.