While I was doing my 10-mile e/w commute (now alas no more) I found that a top-up before the morning start, every three cycling days or so (I didn't cycle every day), was worthwhile. But then, I use a track pump when at home, I find a few strokes easily gets me to my preferred 110psi, whereas as I get older I'm finding a portable pump increasingly hard to use!
And I find that a tyre goes down more quickly when in use.
Note that I'm referring to 700x23 road tyres.