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I personally find it somewhat enjoyable to have some budget constraints to have to work with. Within reason, of course.
With the project I referred to above (Rockies) I really didn't focus all that heavily on my minor league system early on (and it showed, I guess) and certainly stayed mostly out of the Free Agent market, but instead I traded, traded, traded! I was a crazy active trader for the first 4-5 seasons and then eventually got the team I wanted and became a very conservative trader. The thing is, every time I traded I tried to make sure that I not only got decent quality (if only for trade bait later) but also that, whenever possible, my financial bottom line was either unchanged or improved by the trade. It did mean at times trading away popular and moderately successful established players (Andres Galarraga, Dante Bichette, Vinny Castilla) for players who might have appeared to be inferior (a young David Segui, a young Matt Stairs, etc.) In other words, my assistant GM was often incredulous about the trades I made. (Eventually he refused to sign an extension and went out into the market looking for a GM job. As I recall he got one. Then fell on his face and was fired within 2 years.)
But it also freed up enough money to fill some gaps with aging FA's who I was able to get for cheap for 1-2 years (Kirk Gibson, a declining Kirby Puckett) who had their careers revitalized by Coors Field and then got huge contracts for other teams and proceeded to fall off a cliff performance-wise.
Anyway, incremental progress was the key for me. And as the team's success grew bit by bit each year, and the budget followed, and my reputation grew to legendary status, I was able to pour more money into development as well as pick up a few key FA pieces (Bernie Williams, who looks like a HOF'er as he approaches the end of his career in my little universe, Roger Clemens to anchor the rotation) as well as eventually work up to trades that brought me Chipper Jones, Miguel Tejada, Paul LoDuca, Billy Wagner). I was also lucky enough (with very late round draft picks) to be able to draft and develop guys like Josh Beckett and Carlos Zambrano for the pitching rotation.
That's just how it worked for me. Everyone has their own approach and I'm convinced there is no real right or wrong way to do things. (Though probably some ways that increase the chances of success and others that lower it. Pretty sure I did them all along the way.) Do it your way. And have fun!
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