Thanks Nathan for this effort.
I would vote for "shoot for the sky" even if I would like to see "shoot for the moon"

Here is why :
*option 1 is a LOT easier, and you should get it done way faster
*getting everything inside the vmware will make things simple and clear for windows users
*for native linux users, idea 1 will provide almost "native development" and "native debugging"
*There is an ongoing project (esbox) based on eclipse that aims to provide native windows (and linux/mac os) experience. It actually does a good job, and if you ever decide to "shoot for the moon", it would be a better idea to write a plugin for esbox. At some point I decided to give it a try on windows, I used an ubuntu server vmware image, and things went straighforward, (even debugging), but I had finally to switch to a complete virtual version because it was very frustrating to setup and understand how it was working (from a windows user's point of view)

So, what I suggest is to get a QtCreator plugin that shoots for sky.
Later, when you get basic features correctly implemented, you can shoot for the moon.

Good luck ...