As for testing on a Kindle when one doesn't have one, Amazon has a Kindle reader for the computer, so you can load and test in it.
I don't know what version of ID you have but Amazon also has an export for Kindle plug-in for ID. It, as far as my tests go, works well. I don't know the supported versions off the top of my head but you can find the info on the Amazon site.
Make sure all your inages are anchored where you desire them.
Take care, Mike
FYI, The Kindle Fire can use flash and pdf documents. Which can be tested on the kindle via wifi or a USB cord which is sold seperately (why I don't know).
I personaly have tested pdf documents on the kindle, a full page pdf will scale to fit the kindle, the viewer can then drag scale to enlarge the page. As for the kindle format, I haven't tried it yet.
For the wifi, I should clarify it to mean through email. (when self testing)
Based on what I have read in the forum, It appears I would simply need to upgrade to the current version and use Calibre?
You are under a false assumption. There is almost no chance at all that you will simply be able to go from InDesign to EPUB whether it's for Kindle or any other device. If you have no knowledge of HTML and CSS which what EPUB and MOBI use, you are probably looking at a world of frustration.
I strongly suggest that you upgrade to CS5.5 if you are going to be doing this since it does have the best tool set for it, but that's not going to be enough.
Check Anne Marie Concepcion's videos on Lynda.com. If you don't have a subscription, this link will give you a free one week trial: http://bit.ly/fcGpiI
Liz Castro has a couple of books available on the topic and you might want to get both.
EPUB Straight to the Point: http://amzn.to/xQcUSR
From InDesign CS5.5 to EPUB and Kindle: http://amzn.to/wNRj7i
Amazon's site has converters including a beta version of an InDesign plugin for the kindle. It would be worth your time to read through all of there info in creating/publishing a kindle book.