Fall and early winter is when prices for these cars should be at their lowest. You know the condition well and since it's a friend, try to identify a price that would represent a FAIR value that you would both be happy walking away with. Maybe probe him on that before expressing a true potential desire to buy.
If, for example, you'd be willing to pay 15k but he'll be upset if he gets less than 18k for it, I'd evaluate the stress the money would put on the friendship.
If you guys can come to a good arrangement and you get a good deal for being a friend and saving him the time advertising, while still giving him a good price, that's the only time i'd buy....
I know that's not much pricing guidance, just my own experiences in these types of things...
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99 Boxster 5spd - 64k miles
06 Civic SI - 114k miles, D.D., unbelievably reliable and fun to beat on everyday.
08 Legacy GT 5spd - 74k miles.
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