I'd make him a martial rogue (he doesn't strike me as the SA type) the first level to get high volume of skills. Then move him on to fighter for 4-5 levels, then expert for the rest. Maybe a level in Human Paragon to get a couple more class skills if Expert doesn't get the skills you need.
Martial Rogue x 1, Fighter x 4, Human Paragon x 1, Expert x 4.
