It’s not the case. Please read entire thread, thanks… it will make communication easier, although I sympathize with the tendency not to do so.
No - your document would have to set up that way. Sorry. What is your page layout now?
Ah, I see. To make things back up properly, the first page should be blank so page 1 is on the right. Wait, that won’t work either. Let me think some more.
I’m missing something here. Assuming you keep the font size/line spacing the same, wouldn’t the 8.5x11 version be approximately 150 pages?
I say “approximately” because it depends on the margins, which you might want to set differently on the smaller copy. If you don’t and you have 1-inch margins all around on both sizes, the print area on the half-page copy would be 3.5x6.5, or 22.75 square inches of space available to print. The print area on the full page would be 6.5x9 or 58.5 square inches.
If the half-size book is 300 pages, I’d estimate the full-size book to be about 117 pages.
My original intention was to print the original document (which is 300 8.5 x 11 pages in length) to PDF and then open it in Adobe Acrobat and tell Acrobat to print that document to real paper of Page Setup size 5.5 x 8.5. Acrobat would then shrink the print-image that was originallly formatted for 8.5 x 11 paper to make it fit on the smaller paper. The font size and line spacing would not, therefore, be the same.
At this point I have not figured out what size I will make the font or otherwise adjust what I’m doing. The remaining intention is to print the book out to something akin to 300 pages (plus or minus) where those physical pages are 5.5 x 8.5. And to do that, it appears that I will need to print “two pages to a page” and then slice them in half, as discussed above.
I get what you want to do, but I’m still not sure I get what your objective is. If the book is readable when the font/line spacing are reduced to make 300 full-size pages into a 300 page half-size book, why not just reduce the font and line spacing on the full-size copy and reduce the number of pages accordingly?
How are you planning on binding the book? A larger book that is half (or less) the thickness of a smaller one may be easier for the reader to deal with for some bindings.
Ever toted a book around for pleasure reading? Diana Gabaldon, John MacDonald, J K Rowling? Would you prefer a physical form factor of 5.5 x 8.5, or 8.5 x 11?
This is not me self-publishing in high volume. This is me creating a tiny handful of “examples” to put into a select few people’s hands. So never mind how I’m binding it, Staples will advise me.
See if this helps. (I do understand that instead of folding you want to cut the sheets in half, but the printing method is the same.)
EDIT: Acrobat Reader should be able to print to file, so you can create a properly formatted PDF that you can take to Staples.
Before reading this thread, I did not know the term “imposition.” However, faced with such a task myself, I would perform the imposition by hand, after first making sure that each page retained its full text after being shrunk to the the desired size and oriented for landscape printing.
OP, does your printer have a document feeder that will automatically reverse the paper and re-feed it, or do you have to take it in two passes to get two-sided pages printed?
AdamF, that link looks very promising. I can’t test it right at the moment due to the 6$#@@!@#! toner cartridge being out of toner. And of course Adobe Acrobat is uniquely unable to print to PDF.
Expect to be able to test it later on.
Adobe insists that it is able, after digging into advanced settings. Otherwise, a virtual PDF printer is a good thing to have installed.
Home again, with working laser printer.
This technique totally works 
My mother has used this software for over 15 years and swears by it.