As far as I can tell, the main grounds to contest it are along the lines of: that it is invalid ie not witnessed, signed or incorrect information; that the person was not of sound mind, or under duress; that it doesn't meet the needs of legal dependents; that there is another will. I'm sure there'll be others and variances. Whoever the other party is will most likely be keen to avoid the legal costs of defending a challenge, so maybe there's some room for mediation if you can make them believe you have a case?
I know a little about his claim, but not the detail. Always worth a free ‘call your bluff’ letter first I’d think?
Without a doubt, but he needs to make sure he can cite the legal argument and has what appears to be a solid case.