I think one can. Aliases can get mixed up if multiple aliases are pointing to the same URL (I believe the order is random, but of course the last render wins), but I’ve test aliases back and forth, to and from taxonomy pages, and it works fine.
Hence why I suggested using aliases on /best-tools/, pointing to all the pages it would be replacing.
@arikroc, a shortcut to helping us reproduce your steps is to build the test site, and then make it available online. Then we can just clone and run it for ourselves.