I think Hewitt will scrape through for it - but only just. Of course, I could just be being hopeful
but this is my logic - Hewitt has a better record on indoor courts which make up most of the rest of the season, plus he had done consistently well at the Masters Cup. Hewitt's not any defending points from any of these of course, but that's not really the issue - it's whether or not he will do better than Roddick for the rest of the year.
As to who "deserves" to be #2, I think it's extremely close. Hewitt has had a very marginally better run at the slams this year, but obviously Roddick must have had a better year overall or he wouldn't still be ahead in the race. It will be very interesting to see what happens.
Incidentally, I understand what the ATP's trying to do with the Race, but I still think having two ranking systems is confusing and silly.