New stall or balanced flywheel?

I have a 318 in my Dart right now with a 2400 - 2800 stall. I can never remember. I am putting in a 408 stroker soon and got into it with my brother. I was going to buy a new converter in the 3800 to 4000 stall range. He says I won't be able to drive it on the street and should stay with my current stall, in which case I will have to buy a balanced flywheel to work with my internally balanced converter. What do you guys think? New converter or new flywheel? I think I need a higher stall but I always value the opinions I get here.

408 Stroker
Edelbrock Super Victor intake
Edelbrock performer rpm heads (gasket matched w/ light porting)
Holley 750 double pumper
Comp Cam 242/248 Dur@ .050, .3660/.3630 lift @ .050, 112° lobe sep. 549/544 gross valve lift
Hooker Super Comp headers w/ 2 1/2" exhaust
904 stock tranny
Dana 60 w/ 4.10
Caltracs and mono leafs

You mean a flex plate to go with auto tranny, don't you? Fly wheels go with manual tranny. If you are going to drive it on the street probably 3000-3500 stall. I have 3000 in mine. Maybe someone with more info will chime in.