to build on what kktell explained in most excellent terms, the big difference between your hypothetical comparison is WHERE in the torque/RPM curve those 400-500 horses arrive. Yes a built 302 will go 400 HP but you will be up there in the RPMS to find it, and the torque is up there also. A 347, making the EXACT same HP, will bring in the torque MUCH sooner in the RPM range; that makes it a much more street-friendly motor, with much less wear on the motor itself. The leverage advantage of a stroker at lower RPMSs has it all over the stock stroke in my opinion.
Additionally, as with any displacement issue, the smaller the CID, the more money you will throw at it to get the same HP figure. Bigger motors are cheaper and work less to accomplish the same thing, all else being equal (a disadvantage is slightly poorer fuel mileage). A 331/347, properly built, will give you the power of a stout 351 or better with the weight/size advantage of the 302 (the smallest-dimension American small block V8 made).
AFAIK, the oil-ring issues and crank angle issues of the early stroker kits have been engineered out, now that the kits are in mass production and use specifically-made pistons and cranks. Early kits used different rods from diff manus (Chrysler 318 and 2.3 Pinto rods were especially popular)bolted to turned-down Cleveland cranks and the like which did cause oil-burning probs and piston side-loading issues. Almost all kits now keep the piston pin out of the oil ring.
whoa! I just noticed....I talk too much..tell me to shut up next time, willya? ::