Does upgrading the software on the chassis carry over to the guests?

I would be sure to shutdown each guest before upgrading/booting the chassis. I don't know if that is officially documented any where yet, but that is what we have learned from experienece and our SE agrees. Once the chassis/host has been upgraded you can start upgrading you guests. F5 recomends only upgrading a single guest per host at a time to minimize resource contention. As for the image uploads, yes you will need to upload the images to each chassis and each guest. This has changed I believe in 11.6, however. In 11.6 images uploaded to the chassis are available to the guests.