So here's what i have: Factory Bose system w/DVD w/o Nav System.
Im looking to: install a new Head unit with a DVD player and i would like to have my factory DVD player and my new Head unit DVD player to play the same thing at the same time. Is there an easy way to to this? Im pretty open as to what head unit i replace the factory one with. Thanks...

Hmmmm..... There are some threads about connecting an aftermarket Screen to the OEM DVD Player but I'm thinking that the OEM DVD Player might need the OEM HUD to function. If you can get the OEM DVD Player to function with the aftermarket HUD in place (I don't think it's possible but could be wrong), then you could splice an RCA into the Video Harness that feeds the OEM Screen to tap the Video signal to feed both screens but I have a suspicion that you're likely to have to go all aftermarket for it.

Actually im cool with bypassing the DVD player all together and having the new HUD DVD player display on itself as well as the OEM monitor. Is that possible?

The OEM DVD Player feeds some specific connections to the OEM Monitor where the monitor cannot be used with an aftermarket player. I don't remember what those are but BBF posted about them around 6-mos ago. What about replacing the OEM Monitor with a M&D Monitor connected as a second monitor to the new aftermarket HUD and removing the OEM DVD and Monitor???

I'm just trying to re-use and save as much money as possible...

I hear ya.... I know that you could replace pieces in reverse order Monitor -> then DV Player -> then HUD but I don't think it'll work the other way. Hopefully, BBF or llajumpvid or white knight will chime in but I'll see what i can find.