Oh yeah air compressors. One thing different from the job site and your situation is during a day on the job site the compressor will turn on every three to five minutes or more. Basically it's like running it all day long. Even after running it all day long there is maybe a quarter cup of water in a high humidity environment like Portland, OR.
You can drain the tank while the compressor is running without much problem, it certainly won't wreck or wear anything out.
You'll get a feel for how much moisture develops and it won't be the end of the world if it's not emptied everyday.
You may be able to get an inline moisture trap and plumb it between the compressor and the tanks, you should have one before the shoebox for sure, many have a clear cup so you can see how much moisture is in there and the end will have a similar twist thingy to empty it like the tanks do on the compressor.
Be careful with that teflon tape to not get it into the airline. It can clog things if the line or holes down the line are small and a piece of tape dislodges.
Also there is a bit of an art to wrapping the teflon tape, you want to be sure to wrap it so it tightens around the threads when you tighten the fitting. If you wrap it backwards the tape will loosen when you screw the fitting onto the threads.
Also the quick connect fittings have a habit of leaking after they are used. Job site nail guns are always leaking from the quick connect fittings, another reason why the compressor kicks on every few minutes.
Oh and usually the exit air is pulled off the top of the tank and the water will settle on the bottom, I had a Hatachi side tank that had two tanks (one atop the other) and you could practically fill the lower tank with water and the airline from the top would be bone dry.
Seven hours without kicking on is REALLY good.
20+ years in construction, woodworking & auto repairing, dozens of compressors and air tools used during that time. Not one failure to date.