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The 2707 will give me component and composite input for the Wii, and the 1920x1200 resolution to natively view Wii's 1080p.

I've got a 2407FPW and the component and composite inputs are okay but not amazing. A proper TV gives a much nicer picture. The picture looks kind of blurry around certain edges. It is the same on my old 2004FPW.

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Maybe 27" would make DVDs look better (or remain hurt by the Pioneer DVDR drive)

Why does the Pioneer DVDR drive hurt it?

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if I can hack USB2 into my 6 year old machine (my last attempt failed).

If it is 6 years old, what video card do you have? Will it drive the LCD at 1920x1200 with a decent frame rate?

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But honestly, the cost per use on a monitor makes the purchase a no brainer. The 445Xpro cost $800 and lasted 8 years, so make the $1000 2707 last ten years.

It isn't $100 per year. The CCFL backlight tubes in a LCD will slowly get dimmer and dimmer the more you use it. Over 10 years I'd expect it to be around half the bright as what you had when it was new. You can get them replaced but it probably won't be worth the time or money by that point.