I think this does what you want, except I've put in "<stuff>" where you had "$$"-- when I use Perl to tag text I tend to put in HTML or XML-like tags and then use an XML or HTML parser to extract a data structure to stick into a database or whatever.
open(MYINPUTFILE, "<sdnew02.txt");
while (<MYINPUTFILE>){
$_ =~ s/(\s-)$/$1\<stuff\>/;
$_ =~ s/(:)$/$1\<stuff\>/;
print $_,"";
}
You seem to have gotten hung up on worrying about the returns or newlines, when you should have recognized that you needed the end of line anchor. If you want to make the replacement more robust you could put in some matches to arbitrary amounts of whitespace before and after the "-" or ":", but before the $ anchor.
From what you describe, Perl would probably do all the text munging you need. Databases are great for randomly accessing data based on whatever relationships you want to select on, but Perl is hard to beat for dismantling text. Most of what I use Perl for is taking apart text and sticking it into databases for other purposes. Friedl's book "Mastering Regular Expressions" is still a great place to start. There are probably free tutorials floating around the web, but MRE gives clear explanations and gets you up to speed fast.