Take it a chunk at a time 
before you know it your brain will forget how things work in windows to make room for linux knowledge
Wenn it comes to DE’s its really a matter of personal preference really.
But if you are a core windows user, and you prefer the windows like workflow,
then Ubuntu with the Gnome desktop is probably going to get you frustrated.
Ubuntu Mate might be one of the better choices for really new users.
Because their welcome screen contains a step by step procedure to setting,
up your system the way you like.
Caja file manager is decent, and the software bootique gives you straight acces to,
some of the best applications.
Kubuntu will also be a decent choice.
KDE is probably the nicest DE with most customization options out there.
However you can get lost in its settings pretty quickly wenn you’re new.
But other then that KDE has a really nice set of tools and QT applications.
Dolphin file manager is still the best file manager in linux today imo.
Xubuntu and Lubuntu are generally great distro’s for older hardware.
Because they are low on re-sources.
The only downside of Xubuntu and Lubuntu is that they are very customizable.
However you need to do everything yourself.
Ubuntu Budgie: Also nice.
Closets DE to windows is probably Cinnamon.
However if you like an Ubuntu base and you wanne try Cinnamon,
then Linux Mint is probably a better choice.
But that highly depends on your hardware.
You could also install the Cinnamon DE ontop of Ubuntu.