I have a bunch of Sears stuff, but their oilless is not and never will be one of them. My first compressor was a 60 gallon oilless. I was painting an almost new at the time Toyota camry and the basecoat alone cost over $200 back in 1994 I think.. Anyway, base went on beautiful and 2 coats of clear. I was putting on 3 at the time. That compressor died half way through the last coat and Sears service guy tried to pin the fault on me because I had removed the filter after it stopped and tried to tell me I had been painting without the filter. It took me about 4 hours of arguing with sears over it and eventually got my money back for the compressor. Funny thing is I paid cash for the compressor and had to wait 3 months for Sears to mail a refund check.
So I bought a Sanborn very quiet oil type compressor and never had the first problem with it. That old Sanborn was fantastic and could keep up with every cut off wheel and sander I had at the time . The Sears barely kept up with any tools.
Now I have an 8 gallon HF deal. It's not too bad, but much louder than my old Sanborn.
Anyway, I was going to suggest an extension pipe under the compressor that sticks out about a foot from the bottom and paint it some bright color to serve as a reminder to drain regularly. If you have just a small draincock under the compressor chances are it's out of sight, out of mind. An extension pipe is more visible and easier to get to.
I won't do it with the cheap HF, but if I had a 60-80 tank I definitely would think about the extension.
I figured it's time to change my signature so hold your breath. This is it.