A Toughbook for 250? where? I want one
Make sure you have at the very least 128MB of RAM. 256 MB is more like it for a fast response when working with large maps. Also ditch 98SE as anything prior to windows 2000 is unstable. Although they work better on RAM challenged machines.
I've taken a laptop on trips and it's simply awesome

! I've taken a laptop loaded with TTQV, Russian maps, TPC/ONC maps and sat images, and wondered in the Sahara and had a lot of fun with the setup. I even loaded up the notebook with 3D terrain visualization software which creates 3D views from any coordinate I specify by mapping the sat image onto DEM elevation files and compared that to reality

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It was great fun but:
I used it while driving and for the first few times it simply sat on the lap of the passenger. This was very cumbersome and the wires were messy. Later on I fixed it on the dashboard which was much less clumsy but blocked access to the dashboard, hampered ventilation and made my small Jeep cockpit seems smaller.
A project on my list is to take apart the dashboard, modify it and integrate a touch screen monitor in the dashboard and hide a small factor computer behind it. The computer will be fixed in the Jeep and used for mapping and playing mp3. I already got most of the parts needed (wasn't easy) and I'm just waiting for some free time and the energy to do the project.
You suggested in your post that with this setup you won't carry paper maps. As I'm sure you know, computers do break down, hard disks fail, files get corrupted, TTQV crashes and most of all windows simply sucks and you can count on it to simply stop working for no apparent reason. You cannot rely on that setup even with the marvelous Panasonic Toughbook. Even when I use only a GPS, which is much more reliable than a computer, I don't fully trust it since any electronic device can fail. I carry a spare GPS and paper maps. Most important of all write down your location every hour on paper. The backup paper maps won't do you any good if don't know where your current location is.
A neat trick a biker here in Egypt told me is to mount somewhere on the dashboard or handlebar one of those cheap and small calculators with the paper roll that prints out the calculation. Every once in a while punch in your coordinates and there you have it, a paper track log.
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A.B.
OasisPhoto.com – Images from the Magical Sahara.
ShortWheelbase.com – Jeep preparations.
Coordinates Converter – Lat/Long <-> UTM Conversion Tool.