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Done Tilde would be even nicer if {tab,F8,F9}-triggered expansion knew its significance.

The title says it all. I find the semi-recent addition of leading ~ in a pathname to mean "home directory" to be very handy. (Especially so since that has long been true in *Nix shells.) I also find key-requested expansion of pathnames very handy for navigating directory hierarchy. Those two features should work together.
 
I don't use F8 or F9, but Tab knows about it. If I enter ~\des<Tab> it changes to C:\Users\vefatica\Desktop\
 

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