Addressing envelopes by hand is a drag, but sending them through the printer often involves manual feeding hassle and jamming. When I found the Dymo Labelwriter 400, my envelope-labeling problems were over: this baby will pop out an address label in (literally) one second (or sixty a minute, if you want), using a 300 DPI thermal-printing process. The unit plugs into your computer via USB and shows up as a printer; the included software adds barcodes automatically, and allows you to store addresses in an address book for even quicker future printing. The printed material is monochrome black-on-white, and you need to use the use rolls of thermal-printable labels instead of ordinary paper labels, but the Dymo is fast as hell and turns out crisp-looking labels in no time. You can get the labels in all kind of different sizes for different uses, and it’s easy to swap rolls in and out. It works great to print out labels to put on folders and boxes too.
You can even print postage, stamp by stamp or a roll at a time, by swapping in the appropriate blank-stamp label roll and pre-paying over the Web.
I’ve got one Labelwriter at the office and one at home, and I use both of them just about every day.
["Production of this item has ceased and all stocks have been depleted," according to supplier Label City. As of June 2010, there are some new and used units available via Amazon, but it's unclear how long supplies will last. -- SL]