No. of Recommendations: 0
<Reservations are that he is very cautious and needs alot of coaching to do the "right" thing.>

I agree with Pixy that you just need to keep talking, and seeing some numbers might help (if he's the analytical type). However, if you think a less-analytical, more-psychological approach might work, here's another suggestion.

You say that he is very cautious. Looking at the investments you described earlier, he has a maxed out 401k and a regular IRA (that will not be converted), both of which are tax-deferred . His 401k contributions probably exceed the 2k that would be put into a Roth IRA, and since the 401k and regular IRA have been in existence longer, they will probably always exceed the value of the Roth IRA.

Cautious investors diversify to minimize risk. The truly cautious course of action, since nobody can predict future tax changes, would be to go with the Roth as you suggested. This would give him at least a small portion of tax-free investments rather than putting all his eggs in one tax-deferred basket.
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