Upscaling is a bit of smoke and mirrors in many cases, don't assume it offers you anything. But it does offer a digital connect, which has some value. Take some time to get to know your new monitor, because it does it's own upscaling. Upscaling players add exactly nothing to the DVD image, and with the better monitors you will see no difference at all. The main benefit from upscaling players is when they have better upscaling circuitry than your monitor does.

As an example, and since you already have a HD-DVR sat receiver, try inputting the sat picture to the monitor at different resolutions and over different connections, and see how it looks in comparison. Use an HD channel, one with the best picture you can find, and also a plain SD channel with lesser image quality. This way you can get some feel for the monitor's upscaling abilities. On a top-quality monitor, you really shouldn't see huge differences, because most of what is on the Dish HD channels is less than DVD quality. You should pick up small improvements in contrast and color over the HDMI connect, but the image itself shouldn't be hugely different in sharpness. If it is, then you might benefit from an upscaling player. If your current player/recorder delivers an image that rivals what you see on the HD channels, then you might not need an upscaling player/recorder at all.