Well since you could easily sell the extras for more then the asking price it's hard to go wrong.
Extras? I see an X/Y table - $100 if old US; zero if it's Chicom. The center pulley setup sometimes brings $100, but since they can be home-shop-made, I don't value them that highly. What else there adds up to $375?
Without seeing it in person, hard to judge the workmanship. For example, the feed handles and hub could actually be an improvement over the OEM.
Bottom line - for that asking, an inspection, including drill rod/dial indicator to check runout and a close look at the chuck jaws is required.
Since period-correct Craftsman motors are thick on the ground and for cheap, it's difficult to not subtract points for the older motor. Look closely to determine if it's ball bearing. Why so many will throw on a sleeve bearing motor without understanding they're not rated for drill press vertical mounting?
Way OT, but locally we had a guy who worked full time for the Air National Guard. He had access to the surplus from the Guard and Air Force shops, plus the supply bins and time to play. He'd buy broken or non-functioning machines, rebuild them with parts from others or parts he found on his own time. He'd use aircraft grade bolts and hardware, machine up missing parts from stainless. In his case, this $375 drill press might have cost the taxpayer $1500 in parts and labor by the time he had it up for sale.
jack vines