I feel a little dumb asking this but a quick answer from a knowledgable person would save me a lot of time.

When updating and uploading the new dragonfly to my host provider, is it better or even required to delete the old html files and do a clean upload or is it better to overwrite the old html files? I am using Site5 as a hosting provider.

Thanks,
Warden

Well, I would say you should make a backup of all the html files on your site before overwriting anything, that way you can roll back or recover them if you decide later that you want to.

I have heard of one problem mentioned with pre-existing html files causing conflicts when LEO is enabled, but haven't experienced this difficulty myself.