re = /(?!^)(?<!\d[.A-Z])(?<!\d[A-Z]\.)\b(?=\d+(?:[a-zA-Z]|\.)\s+\p{Lu})/
str = '5. SCOPE This document outlines what to do in case of emergency landing (ignore for non-emergency landings) on tarmac. 6. WHEELS Never land on tarmac. Unless you have lowered the plane wheel mechanism. 6.1 Lower the wheel mechanism using the 2 Switches labelled \'wheel mechanism\'. 7A WARNING 7A.1 Do not forget to warn passengers.
'
subst = '\\n-----------\\n'
result = str.gsub(re, subst)
# Print the result of the substitution
puts result
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html