Welcome to the other side 
1) Nope. The size of the system partition has been increased over the years, so a full fresh installation is very much recommended. (Or you can resize the system partition manually with tools like PQmagic, if you think you can manage that)
i use a 1024mb size since all the talks about what the system partition size should be...
2) I don't know all skins that are Kodi 17 "proof", but with a fresh install you will need to install it separately anyway.
3) Basically, yes. Having a good backup is always handy.
4) LibreELEC has recently stopped using SMBv1 by default and starts with SMBv2 and up. You can still force SMBv1 support via a setting. However... In light of the worldwide WannaCry attack, you are very much encouraged to keep your network save, and set your devices/server(s) equally to SMBv2 and up.
5) You should only rename the old databases if you do NOT want to have Kodi 17 upgrade them, and want to start totally fresh. Otherwise, let Kodi do its thing (it may take some time). The old databases will not be changed and not be removed.
just do nothing and it works
If only everything was that simple 