Need to know more to advise! When excatly did he come to the UK and what has be been doing to date? With all R2R cases a chronology is needed.
Basically if he achieved worker staus in past and retained it (eg by claiming JSA) then became ill he can keep R2R during a period of tempoarary illness (CIS/4304/2007).
For permanent right to reside, has to have 5 years continuous residence in accordance with EEA(Immigration) 2006 regs, or under 2000 Regs prior to 30/04/06. If he was a worker or retained worker status, this will count.
Jobseeking prior to April 2006 counts due to CIS/4299/2007 and after April 2006 due to 2006 Regs. Short breaks may be OK due to CIS/1951/2008. You can also use EU Directive 2004/ 38 which refers to legal residence, but this is awaiting clarification in case of Mc Carthy with regard to non-qualified persons under 2006 and 2000 Regs.
I've just done an appeal on permanent residence ( we won, though DWP will try to appeal of course) so I had to get up to speed on the law!
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