A while back, I released the Microsoft Word file Import/Export (Lesson) plugin, which supports importing a Word file into a lesson activity. Each section of the Word file (delimited by a "Heading 1" style) is imported into a separate page in the lesson. This is quite a quick way to populate a lesson with most of the required content. After import, you can change the default sequential page order to whatever you need.
At present, question pages cannot be imported directly into lessons, however, the most recent version of the Microsoft Word File Import/Export (Question Format) allows questions inside Word tables to be imported into a lesson using the "Import question" facility (see screenshot below).