It's difficult to say now, but it's more likely to do than not.
Sooooo, Nintendo Switch has been selling like hotcakes in the past two years. PS5 isn't due out until holidays 2020. With Poke'mon, and Animal Crossing set to release this year, Switch sales are about to explode. By the time PS5 comes out the Switch may very well have 60 million units sold worldwide. And sales for Switch just might keep going, and going up until 2024. So my question is this...
Do you think the PS5 will eventually catch up to the Switch in sales? And if so, how long do you think this will take?
Switch sales are hardly outselling PS4 and it's more likely that Switch is peaking round this year. The following years, Switch will start getting slower. Pokemon may be the end of its peak. Nintendo still rules Japan, but there's not many Nintendo consumers out there to make Switch sell more than 3DS.
The correct answer is we don't know.
That said, it's typical the market leader tends to do significantly worse the following generation. Was true of the PS2 to PS3, Wii and 360 to XBox One and Wii U. You can speculate the reason why but I believe it's because the loser have a better idea of what went wrong where the winners tend to rest on their laurels and make stupid decisions. Sony has had quite a few blunders with cross-play, censorship, their Nintendo Direct thing, and the fact these games are announced years in advance. My expectation is they'll do worse but you really can't tell much without seeing the console and the games.
Even though there's truth to what you say, I don't think any of those things you mentioned would stop Sony to be very successful. Cross-play is more a media bitching than anything else and Sony can fix that if they're not doing it right now. Censorship is a non issue. The few games they censored a bit aren't relevant at all. Their direct thing is just a streaming for enthusiasts and it doesn't change how powerful a release of COD, GTA or FIFA is for Playstation. They could keep doing their direct thing or get rid of it and their demand wouldn't change at all.
When PS4 will hit 100m consoles sold: Before Christmas 2019
There were three ravens sat on a tree / They were as blacke as they might be / The one of them said to his mate, Where shall we our breakfast take?