I'm sure you've seen those huge rectangle shaped bags most pilots lug around. They are called flight kits....and they are very heavy.
The CRJ has a space designed for flight kits. Yes I am a Republican...and proud of it!
Inside, pilots carry manuals that are required by the airline/FAA to be onboard at all times. My flight kit contains navigation charts (made by Jeppesen), a company operations manual, an aircraft specific procedure manual, my headset (the company provides one, but I carry my own), checklists, umbrella, lotion (flying around makes my skin VERY dry), snacks (I never know where I am going....plus delays), pens, batteries for my headset, notepads (taken from hotels, I use them to jot notes down) and finally my Easy button. I weighed my flight kit a few months ago, a little over 20 pounds!
I update my navigation charts at least twice a month. The company sends out an email that a new update is available. The charts are set out in the crew room. In front of each package is a sheet stating the instructions for the update package. The charts inside replace an older chart or are an entirely new chart. Sometimes the instructions are to simply remove charts (like my last one). Sometimes I update 40+ charts. Sometimes just one.
My airline only has charts for airports we are allowed to land at in normal operations, thus I don't carry around a chart for every airport in the United States. In an emergency we can land at any airport. I have three binders for charts. One is for cities starting with the letter A thru cities starting with the letter L, another is for M thru Z and the final binder is for the low and high altitude enroute charts for the entire continental United States, Mexico and Canada.
The time is takes to update charts has been as quick as 5 minutes to almost an hour. The biggest annoyance is when a pilot is on vacation for a few weeks. There might be 3 updates that come out while they were gone. Updating charts is done on my own time. I mostly update charts while sitting airport standby. Some guys do them on overnights. They all have to get done. Flying around with outdated charts is unsafe and a big no-no. In front of my main binder I have a page where I keep a log of all updates. If an AA inspector wants to examine my manuals (which they are allowed to do), they can clearly see how up to date they are.
In addition to navigational charts, I also update manuals for my company operations and my aircraft. These updates aren't as frequent, coming out as needed (normally once or twice a quarter). These are also announced via email and available in the crew rooms.
With all the updates it can get confusing over time if an individual page is the correct and most up to date page. To solve this, every manual has a section with a list of EVERY page in the manual and what the most up to date revision number is of each page. Yes it can get confusing.
Some airlines are switching to Electronic Flight Bags (EFBs) . Pilots are issued a laptop or tablet which contains all charts required to be carried. This reduces weight and the chances of charts getting lost (I swear cockpits eat charts, I have had to reorder a few!). The initial cost is high, but the reduced time it takes to update and distribute update can offset the cost. Right now only a very,very, very small number of pilots at United States airlines have EFBs. EFBs are more common in corporate flight departments and charter operations. They have a much smaller pilot group and thus lower cost.
A quick google search found Navaero as a company that makes and sells EFB's (http://www.navaero.com/t_bag/commercial.php). There has been talk of EFB's at my airline....but so far it's just talk.