I think the reboot will mostly only cater to a niche audience of pokemon and will probably end up making em lose money.
Reboots in general rarely pay off. Pokemon being rebooted would also mean the vast majority of what players own up to this point would be incompatible with the new game, as the Pokemon and whatnot wouldn't exist in the new canon.
Beyond the initial reboot, the only logical way to move the series forward would be to add changes, new Pokemon, etc again. But according to some, players don't like any of that stuff. Pokemon would reboot to Gen 1, then just... go nowhere from there? The series would stagnate.
Best course of action would be to not reboot the main series. If anything needs a "reboot" it would be the anime.
And this is using "reboot" in the sense of a "reset". If they rebooted, in the normal sense, it would mean that they would be remaking the series with a new vision. This means it wouldn't go back necessarily to "Gen 1", but an alternate interpretation of "Gen 1". For example: It would still have Mega Evolutions/Z Moves, and possibly even design changes to old Pokemon; removal of some of the forgettable Gen 1 Pokemon; likely including select post-Gen 1 Pokemon and whatnot. It wouldn't be the Gen 1 that started the franchise.
It would be more akin to reboots in comics. So a rebooted Batman is still Batman, but the rebooted version now has a huge alcohol and drug problem, and sometimes loses control and hurts himself and others. Alfred doesn't exist in this reboot because Batman killed him during one of his rampages.