If using stock heads, and mostly stock 440 parts, then the 440 could be built for less money.
The higher quality parts of the stroker (stronger crank, rods, 7/16"rodbolts, and lighter forged pistons) will support more power than the stock rods, 3/8" rodbolts, and cast pistons. Also the stroker kit comes with a slightly thinner 1/16" top and second ring. The Total Seal rings and bearing in the stroker kit are more performance and expensive than stock rebuilder quality parts.
So if looking for performance bang-for-the-buck would be a stroker.
If cost is the primary concern a stockish rebuild can be done less expensive, but the total cost difference will depend on how much work it costs to recondition all the old parts. Worn out cylinder heads are costly if replacing valves, guides, seats (hardened exhausts), springs, retainers, machine work for dual springs, and such..