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
[download]

So you want

my $qfn = 'C:\img\del me\three (3\00000253.jpg';
system(qq{start "" "$qfn"});
[download]