None of those work. See Re^3: win32 parenthesis system weirdness for why the first doesn't work.
As for the last two, it's due to start's very wonky parameter handling. If the first non-option arg is quoted, it's taken to be the title.
start file.jpg # Works
start "file.jpg" # Doesn't work. Same as following
start "file.jpg" cmd # Launches cmd in new Window titled file.jpg
start "" "file" # Works
So you want
my $qfn = 'C:\img\del me\three (3\00000253.jpg';
system(qq{start "" "$qfn"});
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