Basically, if you want to retro fit a 255 crank into the 21 stud block, you'll need to perform the following operations; shorten the snout and reduce the diameter to suit those of a 21 stud crankshaft. Reduce the main bearing journals to 2.399 to suit the 21 stud block, BUT, you'll also need to widen the front and centre journals to match the width of your sample 21 stud crankshaft. 21 stud blocks have smaller dia mains but the front and centre mains are longer than the later 24 stud blocks. As the later crank runs a positive rear main seal, and the early cranks run a slinger, you'll need to modify the rear of your block to suit a rear main seal. Depending on the style of your existing rear main cap, this can be easy or more involved....Now, depending on what bore you're gonna run, you may need to grind the rod journals to the 1.999 dia and run 21A type rods, you'll need to run 81A style rod bearings, not the earlier flanged style. So there is a cost saving...Should you decide to grind to the 2" journal size, you could offset grind and achieve a 4 1/8 stroke. Or, and I don't know if the rods will clear the block, if you bore to 3 3/16, you could run 99A or 8BA rods. I've always run the 2" bearings and 21A rods, smaller dia gives a slower surface speed, which in my opinion is beneficial. Note though, that the piston speed is increased, and with the shorter overall length of the piston, it is more likely to 'rock' in the bore.
A lot of work, a lot of dollars if you're paying someone to perform the machining operations, is it worth it? you asked. Well I suppose it gives you bragging rights; 'I've got a 255 cu in 21 stud', but in my opinion, having done all this crap, is that a 221 cu in 21 stud, built with a few traditional mods, is far and away better than the bigger cube motors, on account of the rotating/reciprocating assembly being lighter, they are freer revving engines.
Would I do it again? Nah, it was an experiment, and whilst it is a fine running engine, it is nowhere near as exciting to drive compared to its predecessor.