With 5k I wouldn't buy
a pistol, it would be pistol
s.
Glock 19 or 23 gen 5 (whichever if you prefer 9mm or 40) - If you can (would) conceal a 17/22 then get that - $600 and consider the MOS.
Whatever you choose from prior line get another, two is one; have a replacement of your carry - $600
Pocket gun: Sig 365, Glock 43, Kahr PM9 - at least 9mm and it is to be carried with (as a 2nd gun) that primary you chose. $600
Two is one applies to the pocket gun, gotta have a spare - if you wear skinny jeans I guess a LCP is okay, but try harder. $600
So far we have spent $2,400 and we have two primary guns and two pocket guns.
How about a red dot sight? That is why we got the MOS Glock. Holosun HS507 is about $300 but we need two so $600
We have now spent approximately $3,000 and have two carry guns with red dot plus two pocket guns.
2k remaining will cover a Dan Wesson V - Bob and some ammo:
https://danwessonfirearmstore.com/dan-wesson-v-bob-two-tone-45acp-4-pistol/