Computer Guy may be able to reuse your current copy of Windows on the new machine, since you are going to retire the old. Ask about it.
Consider a second, mirrored HDD to avoid unplanned downtime.
Unless you're financing the whole shebang in one go: Keep the old display on as primary until your preferred Samsung comes on sale, then retire it to secondary display. No Computer Guy or special tools needed to switch monitors, though you might need a DVI-to-whatever adapter depending on the old display.
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Consider a second, mirrored HDD to avoid unplanned downtime.
Unless you're financing the whole shebang in one go: Keep the old display on as primary until your preferred Samsung comes on sale, then retire it to secondary display. No Computer Guy or special tools needed to switch monitors, though you might need a DVI-to-whatever adapter depending on the old display.