I upgraded to the latest version of Tortoise and I am looking at the current manual available on your website. Running Windows 10 Pro.
Chapter 1, Section "Checking Out a Working Copy" talks about the context menu
TortoiseSVN → Checkout...
There is no such menu item. Instead, it appears the item is "SVN Checkout..." I tried it and it seems that it works like what the manual says.
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Also, in the Section "Adding More Files", it says
Right click on the folder and TortoiseSVN → Add
In my humble opinion, it is not clear what "the folder" is. It should clarify: "the development folder". An inexperienced engineer would not be clear whether it is supposed to be the original project folder, or the development/checkout folder.
Thank you
Mark