#4 yes, assume you mean turn on from a true power off (or soft reset).
since this is a window system, you would expect a startup folder
just put a shortcut in that folder.
#5 no. (it would be nice, but no).
I find if I turn the power off using the powerbutton, I can't turn the system back on right away... it takes a few secends. if I got impatient, and start pressing the powerbutton. WSOD (white screen of death) will show.
I use psshutxp program to do my shutoff now.