You're correct in your assumption. All bill validators need to be upgraded to accept the new $5 bill. We spoke with a helpful slot supervisor at the Tuscany, who explained that their machines fall into two categories. Some have a chip in them that needs to be physically replaced; others can be upgraded using software in a hand-held device that plugs into a USB port in the validator and the whole process takes just a couple of minutes per machine. They have 1,000 in total and he estimates it'll take a few days to switch them all over. The upgrade software/chips are provided by the slot manufacturer.
Paris/Bally's had already completed the procedure when we spoke with their slot techs and it took two dedicated workers two days to upgrade all 2,400 machines on both casino floors, with other techs also lending a helping hand. The machines didn't all need to be individually changed; in many instances a whole bank can be upgraded simultaneously.
While the old $5 remains legal tender, the machines will continue to accept both notes; only if the Treasury Dept. takes a bill out of circulation will the slot machines need to be upgraded again to reject it.
If you haven't yet seen the new $5 bill, click here for a virtual tour of all the new security features (and for the $10, $20, and $50 bills).