As part of the Spring commissioning, after it had been sitting on the hard all winter I would empty out the sludge and moisture that had settled there. The first cup would be filthy, and the second would be clear.
It's my understanding that such a drain is not allowed by regulations anymore. Too bad; it was a good idea and a lot safer than having a fuel-related failure while underway, probably at the worst possible time. (It was capped with a brass screw cap too -- no way it could have leaked even if the valve was opened.)
My tank hasn't been inspected in the 11 years the boat has been in use, unless the PO did it. I use a 5 micron primary, 5 micron secondary and have a vacuum gage in the line between primary and secondary so I can judge primary filter condition. So far no problems.
I start the Spring season with fresh filters, as routine P-M.