So, I've recently been doing a lot of debugging with Platform Builder on my laptop and with mobile customers who debug on laptops. Sadly, the beautifully light, portable laptops are often XGA resolution. Not a big deal, until you try to see Debug Output, Watch Window, Disassembly, Target Control, Registers, Callstack, etc all at the same time. Then it gets really tight.
Well, the thing that strikes me the most is going to another person's laptop which is using the out-of-the-box PB font settings in XGA resolution. PB defaults to a nice "safe" font selection of, like, Terminal or Fixedsys or something hideous. Ouch. Can barely fit one window, let alone 6. But thankfully it's quick and easy to change under Tools | Options | Format (tab). I run my laptop PB at 7-point Lucida Console for all windows. With ClearType enabled, it's very usable and beats swapping windows to the foreground all the time.
That said, while on the road, I seriously miss my dual-monitor setup back home. In my opinion, upping monitor real-estate is a simple, easy way to increase debugging productivity.