The most readable solution (at least for me) uses just two regexes, the first one shrinks the backslashes and replaces them with slahses, the second one removes the trailing slashes:
my $script_dir = 'C:\\temp\\\\'; print "1. $script_dir\n"; $script_dir =~ s{\\+}{/}g; print "2. $script_dir\n"; $script_dir =~ s{/$}{}g; print "2. $script_dir\n";

You can use transliteration with shrinking instead of substitution in the first step:

$script_dir =~ tr{\\}{/}s;

It's also possible to do everything in one step, but we're entering a golf course here:

$script_dir =~ s{\\+(?=(.)?)}{"/"x defined $1}ge;
Update: Talking about golf, this is shorter:
$_ = s/\\+$//r =~ s{\\+}{/}gr for $script_dir;

map{substr$_->[0],$_->[1]||0,1}[\*||{},3],[[]],[ref qr-1,-,-1],[{}],[sub{}^*ARGV,3]

In reply to Re: Search & Replace repeating characters by choroba
in thread Search & Replace repeating characters by g_speran

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