I don't think you can go back to higher Sony firmwares after downgrading TA-082/TA-086 PSPs.
To allow the downgrade, some keys are changed in the idstorage (or something) and unless you change them back (which I don't think there's an app for at the moment), it will brick when you try and upgrade to higher Sony firmwares.
I would recommend upgrading his PSP to either
3.40 OE-A or
3.52 M33 (both are newer custom firmwares) so that he can play the newer games.
Tell him it would brick (be permanently broken) if you tried to downgrade to 1.50 then update past a certain firmware (maybe 2.71 I'm not sure).