Without trying to get in a pissing match. If it were me, I'd try the 255 cams with a canned map. Free cams, few gaskets, canned tune and time and he is out $100 if he does his own labor, $300 if he uses adjustables. Other option is to change cams ($300+), Dyno ($400), etc. adding at least $700 or more to the costs. I'm with you if he is paying for labor and a dyno, then he should consider a bit better cam, but he can change cams out in his bike using the parts that he has with just some time and a few gaskets for right around $100 and be plenty happy with the bike.
I have a softy with the 103" and 255 cams. I love it. Stock it was pretty lethargic but with the cams it runs great and has plenty of power. Power range is great for touring. I'm not running high RPM's and racing and thats exactly what the OP says that he runs as well.
To the OP. Two things to really look at are the cam lobes and the lifters. To keep things on the low side of cost, Comp cams 850 lifters are great to use and I have yet to read of them failing or having issues. Since your bike came with the HD "C" lifter I would seriously consider upgrading them. I've had two bikes with frosting issues on the rollers.