Before holiday 2019 kicks in, a 50$ price cut. Then another one to 200$ by the time the PS5 and XBnext gen release to be half their price.
That's a good strategy. But, I doubt the latter will happen since PS5 and the next Xbox will likely launch in 2020 and I find it very hard to see Nintendo cutting the price again just one year after they already did. However, I think a hardware revision or a different bundle like a Switch Lite or a dockless Switch would easily sell for that price, if not less, putting it comfortably within the handheld price range.