Antenna
Now, back to your antenna question, yes, you could put a weighted stand on your roof with a vertical. There are a few options from
DX Engineering. As for a vertical multiband, while not ideal, this
Comet CHA-250B has good reviews by some of my friends for roof mounting. It acts as a shortened end fed antenna.
As for grounding, to keep from drilling in your wall, you might want to consider one of
MFJ's Window Feed Through Panel to get the coax into the house. Still use a quality polyphaser and a ground rod.
I hope this helps answer many of your questions and gives you a few things to research. I recommend starting a spread sheet with prices/part numbers and descriptions for every single piece and part you will need to put this together.
SELF EDITED.....