What I've evolved to is a hybrid approach using both a small laptop and keeping vital data on a separate USB/solid state disk. I also currently have a small netbook and would recommend one of them with solid state disk. Here is some of that evolution on some of my largest trips:
~1992: Crossed the USA with a Sharp 286 laptop. Did the dialup thing with acoustic coupler modem from motel rooms. Uploads predominantly of text-based emails. Protected the laptop with extra foam and a large waterproof bag. Laptop was fine during the trip. Eventually some time after trip the display cracked.
~1997: Crossed Canada with a HP Omnibook 800 laptop running Windows 95. Did the modem thing including acoustic coupler modem but more phone jacks. Protected the laptop with foam and waterproof bag. Laptop was fine during trip and still ok.
~2001: Circled Australia and crossed USA and more for one year cycle trip. Used Sony Vaio and also auxiliary Pocketmail device. Primary frequent updates were via Pocketmail phone connection. Less frequent updates were from mini-Zip disks that I mailed home. Father maintained web site from daily emails plus every 2-3 week web page updates that had been mailed home. Laptop disk died part way through Australia. Replaced disk and did a system recovery.
~2007: Crossed EurAsia including crossing Russia. Also followup trip 4000km across China. Used small Sony that was essentially a $$ predecessor to netbook generation. Protected laptop with foam and waterproof bag. Laptop survived fine though after trip the display cracked. Did not actually connect the laptop to any wireless network in Russia. Instead, did local editing and then transferred main content to more than one U3 thumb drive with secondary storage. When we got to a major city (every ~week or two weeks) took the USB drives with me to an internet cafe and uploaded content to web sites. For the most remote parts of Siberia (but where every 1-3 days we might cross a town along the trans-Siberian railroad with cell phone service), also provided very short updates via cell phone SMS message -> twitter -> web site with short GPS coordinates and oneliner type messages. One of my USB drives failed and had to be reformatted.
Last week I cycled 575 miles through Texas from Brownsville to Dallas. For my more local US touring, I'm using a small netbook and relying on wireless uploads.
If I were to leave today on my next third-world tour, I'd likely:
(1) Use a small netbook type laptop with solid state disk. In addition, as a bit of a tech geek, I'd be able to boot Linux from SD card and carry two backup copies of the operating system on an SD card and/or be able to restore my solid state disk with OS from SD cards/USB. I'd keep some extra copies of my main data e.g. photos and videos on separate and redundant USB drives.
(2) I'd separate the OS platform + tools from my data. Keep redundant copies of both, e.g. restore disks for OS and/or booting from SD cards; keep my data on at least two copies on separate USB flash drives.
(3) I'd look at how frequently I really need to upload info. If not real frequently, I'd probably avoid using my laptop be the communications device I used for uploading and instead rely on internet cafes and other things and not connect the laptop to networks. (Uploading lots of large files like video and/or trying to do frequent uploads might add a fair amount to your trip costs as opposed to waiting until you are back to upload some of the largest pieces of info and instead using web pages + photos initially). If there is cell phone service, I'd get local SIM card and be able to send short SMS including GPS coordinates and short update.
(4) I wouldn't go as far down the "rugged" laptop area as some suggest here but instead go more down lines of redundancy of OS even to point of having second netbook back at "base camp" if that made sense. I would keep my data on more than one removable USB drive and be able to use redundant communications including relying on local internet cafes for some (all?) uploads.
(5) I'd find someone on the home front if possible to help receive some incoming posts/blogs and help admin that if necessary as well.