Sounds like the sequel to "her". Guy dies, clause in contract allows use of his data as new OS.

As described, the manipulations Selene makes to Ed's memories sound very camp, like something from a John Waters movie.

Really--"her cute thrift-store outfits leave homeless people with no choice but to 'wear the unfashionable, baggy cast-asides'" is something I could imagine being spat out by Mink Stole.

@1 also seems a little derivative of "eternal sunshine of the spotless mind".