My first inclination is to dismiss this idea for being counterproductive. A 5.7 Hemi will outperform a stock 440 in acceleration, mileage and durability. It weighs less.
Then I started thinking about all of those V6 Challengers out there. An aluminum headed 440 with aluminum intake and a Sniper fuel injection setup could be pretty cool. You'd have more power than the 5.7, gobs more torque and it would be an engine that you could fix yourself. The Interior wouldn't need to be gone through, the body should be in better shape and the suspension gives a nicer ride than any old rusty musclecar. In short, the "buy-in" of $5-7000 gets you a pretty good starting point. People put aftermarket gauges in old cars so that isn't really an obstacle. Heating and A/C would pose some problems but a crafty guy should be able to devise something from Classic Auto Air or Vintage Air.
No anti-lock brakes? So what? Old cars don't have them and people survived without them.
The real hurdle is emission testing. Technically, it is against Federal law to alter or remove the OEM emission equipment. It makes no difference if a state does no inspection or emission testing, it is still illegal to remove the stuff. I get it though, if they don't check, it is highly unlikely that a Federal agent is going to apprehend a guy with a 2009 440 Challenger.