Flint, the age old question is "what type of riding will he need it for?"
Long trips? Water cooled six speed
Combination of Long trips and town... dual sports work best..
Just in town and few trips.... S40 (650 savage)...
And that is the cruiser side... there are sport bikes that can do the same...
If he is a first time rider.... don't go big.... go used and small.. (for the first riding season), you can always resell and go bigger next season.
I have a LS 650 and a small 300 ninja.... love them both.... if he wants speed... tell him to wait....
He can bob or café the S40 with a few extra bucks.... if he wants a sporty looking bike, look at the smaller sport bikes, I talk up my 300 ninja because its fuel injected, water cooled and gets on the average of 65+ mpg (if I don't slam the throttle at every light) with a 4.5 gal tank.
If he didn't get one right off the bat, means he is smart about his choices.... and your choice of the S40 as a "get back on it" bike... is good too... LOL...
Good luck in your endeavors