I once did some insane shots of a ball point pen by hooking everything I had up at once. The thing is most methods are hampered by practicality;
1) Teleconverters - you lose a lot of light each time you add one, plus whilst they are highly corrected optics adding each one adds a lot of glass each time so you end up losing more and more optical quality.
2) Extension tubes - these very quickly become unworkable. Not only does their length end up putting more strain on the mounts (because you've got a DSLR one end and a heavy lens the other) but also the long length makes it much harder to work with - same is true of stacking bellows units.
2) Close up lens attachments/diopters are potentially the best approach as you can get higher increases in magnification with less optics than a teleconverter. However the downside is that, like extension tubes, the more power you add the closer your point of focus gets - eventually you can't increase it any more without the point of focus moving inside the lens.
In most practical terms 3:1 is oft what most need - 5:1 is getting extreme and anything beyond that gets much much harder to focus, hold steady and light to get a good shot.
Practically speaking you can probably go higher if you've a very solid tripod setup. 10:1 is possible (MP65mm macro with 2*TC) and you can go higher still but it gets hard. It's also important to realise that the higher your magnification goes then typically the smaller the aperture becomes, this then means that diffraction becomes a much bigger issue. The MPE 65mm macro at 5:1 is oft used at f5.6 because to go any smaller the effective aperture (which is already much smaller than f5.6) causes significant sharpness loss from diffraction.
I forget what this magnification was but it was lots these are the full shots, no cropping from a crop sensor Canon DSLR