Your 1st paragraph answer of “employee contributions”.
-What is the max dollar amount or % of salary can he do each year?
-Let say he put in $1,000 and before he can take any action it earned $1, can he ask employer to roll $1,000 + $1 (tax free) to Roth IRA?
-How can he find out from employer that $1,000 earned $1?
-How many times can he repeat put in & take out each year without wearing out welcome mat?
-Are all employers required by law to accept “employee contribution” & roll out to Roth IRA?
-Why some companies do not offer Roth 401k?
-When file tax return, any reporting need by him and any supporting report/statements from employers?
Your 2nd paragraph answer
-Can he wait for 10 or more years after quitting and still under 59.5 to do?
-What if the company is out of business/bankrupt, etc before he take any action? Would he lose anything?