As a bare minimum I would probably get these calibers in these brands;
2 .45 ACP pistols -Para compact and full-size
.45 ACP Mech-Tech CCU for 1911
12 Ga. shotgun - Rem. M11-87
5.56mm AR-15, 20" flat-top - ?
.22 rifle - Ruger 10/22
.22 pistol - Ruger Mark III
.44 Mag - Super Blackhawk 5-1/2"
Then when I get around to it;
.380 PPK
9mm pistol - compact ?
.357 Mag D/A - GP100 4"
.22 WMR NAA Mini with .22 LR cylinder
.22 RWS Model 52 air rifle
30mm ammo for PegLeg
I wouldn't replace my Contender and spare barrels. I'd use that money for ammo. No more 20 gauge shotgun, and only one each .22 rifle and pistol. Probably no more lever gun or other deer rifle.