Not as often as I should.
Perhaps you didn't fully read my post that finished with this: "Seriously, this little gadget works great and is a lot easier to manage than a c-clamp.
So my suggestion that that using a c-clamp to push the caliper back in could contaminate your system was partly in jest. However None of the many manufacturers procedures I have read mention a c-clamp. Most have a part # referencing a specific tool to retract the calipers. So a c-clamp is usually wrong but most DIYers use them. The biggest problem with using a c-clamp is that you can't always get them to press on the center of the piston. Scoring, cocking the piston and tearing the seal are much more common than pushing dirt backwards to damage another component. Several manufacturers recommend changing your brake fluid as often as once a year to reduce the chances of corrosion. So that could mean a fluid change more often than your pads are changed.
Do I use a c-clamp to retract the piston? Almost exclusively. Do I flush my brake fluid and replace with fresh annually? Nope. Can using a c-clamp to retract a piston damage your brake system if the bleeder isn't opened? Yes, but you probably have a greater chance of breaking off the bleed screw than damaging something else by not opening it.