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1. For someone just starting to do macro, I would not recommend spending a lot of money on macro gear. Many people that try macro find they do not have the patience for following the discipline required to get excellent macro results. i.e. Best results are usually obtained by using a tripod, low ISO, slow shutter speeds, and high f-stops. Those that go around shooting handheld often get worse results.
...Yet almost every excellent macro photographer on the macro forum shoots handheld, moderate shutter speeds at lower f stops. Go figure...they're doing it all wrong!
3. In addition to the macro lens, buy a set of Kenko extension tubes. They will allow you to get greater magnification with your macro lens, and you can use them on any of your other Canon lenses to get closer to your subject. You can use just one tube, a combination of any two tubes, or all three tubes at once. The best macro photographers do not use teleconverters for very good reasons. If you need to move further away from your subject, use a different macro lens or put the tubes on another lens.
You're right, no great macro photographers use TCs and they all switch lenses constantly in the field.
4. You will get better advice on the Macro Forum than on this forum.
5. Go over to the Macro Forum and look at the EXIF of the best images.
While I agree the macro forum is the best place for this type of advice I don't think looking at the EXIF of "the best images" will help the OP, in fact most of the high caliber work seen there is shot with a wide range of lenses and cameras, some of which the OP, as a newbie to macro, should avoid (i.e. MP-E 65). I will also advise against any macro lens with an extending barrel, simply because they can prove cumbersome and frigidity to use with a flash that isn't fixed or trained to the end of the lens barrel, especially for field work. When using fixed barrel lenses you do not have such issues. In addition, I believe longer lenses on FF are better for newbies as they provide more working distance to interact with their often flighty subjects. A mere inch can be the difference between getting the shot and startling the subject.
Buying used isn't a bad idea, but keep in mind these lenses, especially when taken care of, retain their resale value very well, and there is always a market just in case someone decides macro isn't their thing. One thing I noticed that wasn't spoken about in the thread, but was mentioned to the OP via PM, is lighting. This is far more important than deciding between lenses. With that said, for anyone lurking, be sure to check out the 'Post Your Set up' thread in the macro forum for lighting ideas and tips--this may take your images to a different level.
And FWIW here are a couple handheld shots using the Sigma 150, with or without TC and or tubes...
Edited on Mar 20, 2013 at 04:51 PM · View previous versions