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What 500 do you have (just out of envious curiosity)?

Canon's 75-300 doesn't have the hottest reputation, but a good 70-300 lens is suitable for use with either diopters or extension tubes. Kenko sells electronic extension tubes, that are relatively cheap, and will allow electronic functions (aperture and AF), though you will likely want or have to manually focus at very close ranges. You have to have electrically enabled extension tubes to use with a Canon EF lens, all (normal, non-wacked out) EF lenses have an electronically actuated aperture mechanism, which needs an electronic connection to the body to function.

Reversing rings tend to work best with a good prime lens, old manual focus FD or Nikkors can be had for cheap, and will work fine, given that you will be all manual with a reversing ring, you'll need a doohickey to actuate the aperture lever, though. You can also reverse a complete lens on the front of a longer lens, it will act as a really powerful screw in diopter.

Relatively good Macro lenses can be had starting in the ~$450 range (Tamron 90mm). Longer (focal length) is better for shooting stuff outside that you want to be as far away from as possible (like bugs that will run from you), but you don't want too long a lens for shooting indoors in more cramped space (my Sigma 180mm Macro is way too long on a crop camera for shooting frog sized stuff indoors).
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