In the end budget considerations have limited my choices to two high quality firearms. Eventually I'll have a few, but a man ought to start somewhere.
The rifle part of the equation is settled. I'll get a CZ 422/455. However I'm having a hard time deciding between buying a handgun first or a shotgun first.
If I were to pick a shotgun, I'll probably go with the better ones in the $500-600 range (think Mossberg 590). If I were to pick a handgun I'll go with a really good .22lr (say Browning Buck Mark UDX) or possibly a good 9mm (like CZ 75, but the 9mm option definitely stretches the budget).
What would you recommend? The answer to "It depends on what you want to shoot." is that I want to shoot all sorts of things at the range (and eventually get into hunting). It's only a matter of picking something first.