"Water" seperators are used on boats & aircraft...not sure what you're refering to either, except that unit behind the dr. seat, in front of the wheel-well on side wall. I've not seen a rig with all that stuff still hooked up. It made the EPA happy but as to any real function/help....who knows.
Like Seabronc says.., not likely a problem causing unit, nor is a fume canister.
Fuel pumps have a "weep-hole" on the bottom. Usually when the diaphragm fails, fuel runs out that weep-hole leaving a trail.
They can get weak however & as Seabronc said , visually watching it fill a jar/container is a good test. 1/2 a minute for 1 pint is a good rule of thumb.
They have check-valves in them..., a small bit of stuck debris can stop any pressure build up.
You didn't mention the carb. Did you check the needle & seat..? (could be stuck shut) Can you see fuel squrting fr. nozzles when operating the throttle by hand..? If so, RU gett'n spark.?
I think a vertical sitting filter would fill. I have a couple horizontal/clear filters & they change fr. full, to 1/2 full, to empty as they so choose..?? My rig never misses a beat so I assume the bit of air just never goes away. My neighbors rig does the same thing..