If all I had to spend on handguns (not ammo, training, accessories, etc) was $2,000 I would choose 2 $1,000 guns or 2 $700 and 1 $600 gun.
First, they would all be slightly used.
For 2 $1,000 guns, I'd choose a Sig all stainless Elite 226 in 9mm and a Boberg XR9-S
For 3 guns totaling $2,000, I'd choose a Sig .226 9mm; CZ 75B 9mm mat stainless; and an STI LS40.