I look at the cost of the stroker kits, and subtract the costs of reconditioning and balance the stock crank, rods, replacement pistons, rings and bearings. Usually a stroker kit add less than $1,000 to the short block build.
The heads and valve train is where things can get expensive. Trick flow heads are pretty nice and can be ordered with different valve spring packages that should work with most street cams. This can save money compared to having to change out the valve spring package on heads that only come with one spring option. They also are CNC ported saving time and money that you might spend sending out other heads to be ported. The recommended rocker arms are expensive, not sure how to get around that issue?
As mentioned the 4.25" stroke kit with 2.20" rod bearing (GM) type rods fits easy with just a bit off the oil pickup tube boss, and you can still use the internal oil pickup tube.
For lower RPM, mild street (600 HP), the Trick Flow 240 head (standard intake port size) is nice, and the larger 270 head is good if you are looking for more higher RPM power 700+ HP.
I have used the 440 source stroker kits. You do need to check the fit of everything, and file fit the piston rings.