Yep. For airlines and commercial flying, flight crews pass through a lot of places with good wifi all the time- the random hotel each night, swing by the crew lounge if the airport is a company base, FBO if your operation works out of that side of the airport, and last but not least hitting the update button when you're at home before you head out the door to work.
The updates on the popular Jeppesen app run anywhere from about 10-100mB and only takes a few minutes on good wifi (like hit a couple buttons on the iPad and it's done while your'e still taking a shower). Sometimes there's a little update once a week but the big updates are every two weeks. That's a little different than the "pubs Christmas" routine at the squadron of a hundred pounds of paper charts arriving every 28 days.
Makes me wonder if naval air adopted these how much wifi squatting we'd see at the on-base Starbucks and Subway- whether guys sitting in the parking lot or carrying their company iPad inside while they buy a couple macadamia nut cookies or a cup of coffee.