Like many programmers, I try to be as specific as is practical. This means that I try to make the compiler do as little work as possible by having my code as simple as possible. So for strings, I use the simplest method that suffices for my needs for that string.
<<END
For strings comtaining multiple newlines,
particularly when the string is going to
be output to the screen (and thus formatting
matters), I use heredocs.
END
%q[Because I strongly dislike backslash quoting when unnecessary, I use %Q or %q
for strings containing ' or " characters (usually with square braces, because they
happen to be the easiest to type and least likely to appear in the text inside).]
"For strings needing interpretation, I use %s."%['double quotes']
'For the most common case, needing none of the above, I use single quotes.'
My first simple text of the quality of syntax highlighting provided by a program is to see how well it handles all methods of quoting.