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I save 16 "recent files". They are all listed under "File". The list is using only one digit for shortcut for all 16: 1, 2, ... 8, 9, 0, after 0 comes 1 again. I suggest using letters instead of numbers. Or use numbers until 0 and then continue with letters.

These letters/digits are keyboard shortcuts. Using letters or two digits would present trouble for the standard menu shortcuts.
If you are always using the same files have a look at workspaces. See TP's help under "How to Use Workspaces: Overview". HTH

What I find slightly peculiar is TextPad's method of counting, which goes from 1 to 9, then from 0 to 9. Why not start with zero? And why no numbers greater than 9? (The numbers could easily be right-aligned to keep a nice-looking layout of menu items).