Eh. They've been great at that but I dont see this as it. Handheld stuff is cool and popular right now. Don't get me wrong, they definitely could self sabotage here. They 100% did with the vita and their egregiously expensive memory cards....
But the PSP and Vita were great devices aside from that. I could see this working
Vita was technically impressive, far more capable than the DS. I've got an OLED Vita and I'm amazed how nice it still looks.
But the Vita inevietably lost to Nintendo because it struggled with popularity, and therefore struggled with number of games made for it. It's a catch 22.
If Sony can make a portable that plays all your PS5 library (without needing to buy any of it again) then they might actually be on a winner.
Microsoft has the Edge here (see what I did?) when it comes to handheld, because they already have a weaker hardware that games on Xbox must be able to run, the Series S. This baseline could be used as a handheld compatibility (at least from performance perspective). Sony on the other hand has a monster console and no weaker version of it. So there is much more and longer to developer. For the coming years, I'm not convinced Sony would be capable of doing that. Also imagine the price it would have.
I don't think Sony wants a PS4 handheld while Microsoft has the newer generation Series S based handheld. Sony wants to sell new games, not the old one.
Read my comment if you like speculation and future prediction.
It's a bit too early to talk about this. First the Switch 2 will come out, then probably Steam Deck 2, then Xbox Portable and only then Sony is ready to release. At that point its already in the middle of the Switch 2's life cycle and the market is full of handhelds. If Sony comes up with expensive prices again, it will be a tough sale (in the long run) and it ends up being a similar failure (for units sold) like the Vita.
The Playstation Portal just streams and is already 200 Dollar. It's basically a tablet with controllers attached to it, but less capable. If Sony goes the route of Apple and markets the Playstation Handheld as a premium device for hardcore fans, then do not expect it being cheaper than 500, around same price as the original PS5. I hope Sony will surprise me.