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Process and Considerations for Upgrading ASA and ASDM?

Good day folks

This month I am going to upgrade our Cisco ASA and ASDM.  I want to go from ASA version 9.6(1) and ASDM 7.6(1) to the latest stable version of both.  I have a few questions.

1.  What is the most current, stable and inter compatible versions of both the ASA and ASDM?  
2.  If I see ASA Firepower tab located in the ASDM, does that mean I also need to upgrade a corresponding file for this as well?
3.  Can I do a direct upgrade from the versions I have to the latest versions, or do I need some intermediary version?  I hope this is not the case.
(4).  If so, are there other considerations, like changing the startup and running configs in some way to be compatible with these newer versions?
5.  Is it as simple as logging into the ASDM, taking a full backup and then tools --> upgrade software from local computer, ASA and ASDM images separately and then setting them to boot images?  Note I prefer the GUI to command line as I am mild/moderately dyslexic, and if it can be done in the GUI, why not.  Save running to start up config, reboot, profit ?
6.  Is it ok to leave the old versions on there and is switching back to them as boot images in emergency ok to do?

I have only even done this once before and it was years ago, with an older now EOL version, with a non complicated running config, and I can't remember.  I do remember it was a non issue, but this is Cisco.

Thanks again for the advice and feedback.
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Miles M

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Thanks Miles for the very detailed feedback, it was invaluable.  I was able to upgrade the device without too much issue.  Have a great week:-)