I like this version the best. I think 4 doors work best as mild customs IMO. Your Plymouth has the same color scheme as the NYPD patrol cars of the '50s and '60s: http://www.policeny.com/rmps1950s1.html
Most attempts to make a 4 door "cool" actually have the opposite affect. That is a nice old car and they run smooth and cheap, ride like a dream, why mess with any of that. Good brakes, seat belts and maybe some power door/window locks for the back seat.
BlueSkies did a lot more than some simple engine bolt on's. His car was amazingly well done, and he went through it with a fine toothed comb. He sold it not long ago, but I'm not sure where it ended up. His page is a great resource for anyone building one of these old boxes. Even though I'm sure that dude has long since forgotten about this post and has no idea of the amount of necromacy it took to bring it back, you made a good point about these cars not being worth very much. I think in fully restored condition they rarely bring more than 10k. It's a very achievable way of getting into a kustom. I bought one and, nosed it, decked it, shaved it, welded the hood seam up, and plan on choping it and doing some body mods. It's a cheap canvas to learn on and not too many people are gonna bitch about loosing a 49. Here's one that was chopped pretty well over on another board some years ago. Dude lost interest and I'm not sure what became of it.
As nice as your car is, I would just lower it a little, add some astro supremes with skinny whites, and roll it. Here are a few pics of my old 49 Dodge. I really mis that old mopar.
I don't know about "cool" neccessarily but classy definatly. This is my 52 dodge that I've cleaned up and am in process of extending rear fenders and skirting.