Hi Ariel, I was hoping that turning those two settings on would make the difference between seeing frequently used items, versus being able to see the recent items that you're trying to get listed there.
Here's another possibility: There is a relationship between the recent items listed in your Jump List and the recent items listed in your Start Menu. If you look at the Recent Items list in your Start Menu, does it have "recent" items, or the same "frequently used" items that you have in your Jump Lists? If it's the same problem, maybe the solution (to both) is to attack the problem from the Start Menu's perspective, rather than the Jump Lists.
Also, there are quite a few tutorials on 'customizing' your Jump Lists. Would it be worth it to take a look at them to see if somewhere, buried in the text, you might find a clue as to what you could do to make the change?
How to Create Custom Jump Lists in Windows 7
How to Create your Own Custom Jump List
Jumplists: Another Handy Jump List Creator For Windows 7
*Using Jump Lists to open programs and items
. (Video from Microsoft that talks about the relationship between the recent items in the Start Menu and the Jump Lists)