I've toyed with this idea before, even swapping in a V10, but the best I could figure was that it was awesome, but impractical.
A 360 can be stroked to 408 or even 426 cubic inches, there's plenty of aftermarket support to make either put out all the power you could really need, and you can do it all with the factory fuel injection (minus upsized fuel injectors) without having to re-engineer anything. Just have to reflash the computer to work with your setup, but that's another matter.
I don't think you can directly hook up the 46r to a 440 RB block. Maybe there are adapter kits to do so? At either rate, a mild 440 is going to put out way more power than the transmission can handle for long. The 46r can be built to take some pretty beefy power, but obviously, you're going to have to budget that in.
For that matter, if you have the 46re rather than the 46r, it shifts based on computer inputs. If you ditch the computer and go carbureted, there is no way (that I can think of anyway) to make the electronic transmission work. Then there's the gauge cluster, which gets all of it's inputs from the computer. You'll have to yank that and install gauges that work with mechanical input, and I, knowing nothing about that, won't even try to guess how to make that all work.
I'm not sure the weight difference between a 440 and a 360, but it might be enough to warrant swapping in 2500 coil springs up front to handle the extra weight.
Probably other stuff I've missed. Can a big block swap be done? Yup. Is there a shortage of hurdles/issues/complications to deal with to get it done? Nope. Would it be pretty sweet if you could pull it off? Oh, yeah!