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i unfortunately can't run at lower than 1440x900 because that's the resolution i use on my work machine to develop with (i remote control the work machine from this box). For software development, higher resolution = more screen real estate = more effective programming (for me, anyway). i hate running at lower than 1600x1200, but my work machine (a laptop) can't do higher than 1440x900.
I remote my laptop (ssh -X) without any discernable issue. X should know when it sets up the driver in the laptop that it has a new screen to deal with...or at least that's how I thought "termcap" worked. It's been a few years since I had any issue in that regard.
While text (e.g., in this mail) is a bit fuzzy, my desktop looks fairly okay, as do videos. That is: graphics looks reasonably good and text looks so-so.
I'd try native on your desktop, then see what you get from the laptop (in case you haven't thought already to try...). But if you are "used" to a 4:3 desktop, a 16:9 might not be comfortable. Oh, I'd ssh from a graphical console, not from Alt-Ctl-F2. That would send the wrong termcap I think. Good luck Tom