I would love a PS5 Portable. I would play it all the time, where I have not touched my PS4 in months except to play DVDs for my kids. It's not for lack of games, but that TV is either used by my family to watch something or I'm somewhere else in the house watching the kids. I've gotten tons more mileage out of my 3DS and Vita lately.
I thought the PSP and Vita were great systems and just didn't find the support that Nintendo gets. I'm not sure Sony would try portable again after getting burned on the Vita. It's more likely they will wait and see how well Switch does in the longer term before announcing their own version. I do think we are at or nearing the end of the stand alone home console 'generations'. The technology is just way to advanced and changing too rapidly to put out these high priced gaming-only boxes that are meant to last 4-5 years. Also, graphical fidelity is nearing a peak meaning raw power improvement is not the most major way to define a 'generation' anymore. However, I think Sony and Microsoft may be going more towards the PC market with an all-around powerful product with upgradable components rather than a slick home/portable hybrid like Switch.