Welcome to the asylum. When did you stop taking your meds?
You're OK with giving up the Charger?
A deuce can work as a daily driver if you don't have too far to travel and have a tolerance for it occasionally being cranky.
You need to be prepared to pull maintenance and buy parts on it's schedule, not when it's convenient or the weather is nice. You still will need another way to get to work when (not if, when) the truck is down for parts or maintenance.
Snowy roads, especially hilly ones would tend to argue for better than stock tires (chains, too) and an abundance of patience when driving.
Since you will need this truck to be ready to drive when you buy it you will likely be better off buying one from a dealer or knowledgeable private owner who has already been through the truck. Either of those options are unlikely to fit the budget.
Where you have some leeway is in the upgrades like heat, better wipers, a hardtop, muffler, locking hubs etc. In any case there is no guarantee that you will have a reliable daily driver and fit it into the $5-6K range.
Be prepared to replace all the cab weather strips and seals.
Lance