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I can agree with the idea of "You "build" a bird to fit the new requirement." rather than preparing ahead of time. Thats the way you actually play the 1st playthrough now, as you don't really have a choice. And given your budget is very limited early on, it makes sense that this is how you would evolve. And to be honest given the limited and randomised access to birds its difficult to fully do it.

The problem is that the difference in practice (given the current status of contracts/birds available etc) isnt that big. Like preparing ahead of time just requires you knowing  that certain cutoffs are very important and stats between them don't add much value. To put an specific example, something I did in following playthroughs once I knew the contracts was not buying ravens with much more than 600 km range. That alone meant that even with my limited budget I could get some that lasted me until the end game. With pigeons it was similar, knowing 1000km is enough for most things, I focused just on other stats and only went for the longer range ones when I had a bigger budget to buy the good ones that can do those hard contracts.

But thats more a balance problem than a design one most likely. In a "full game" (not like this isnt really even if limited in scope hehe) I guess you could have a more clear  progression easily, that could even affect the birds offered. to aid that progression better. You would start with varied but overall easier contracts to complete (good ratio of time/range) but that still require birds with varied skills, and where versatility maybe is more important, and as you progress the ratios tighten and you really need to either build more specialized ones, or pay a premium to get some that can do the hard contracts and yet be versatile.