Drebel with a FF sensor (plastic body, pentamirror = lightweight)
100-400/4.5-5.6 L IS mk2.
100-400/4.5-5.6 L IS mk2.
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Canon 17-40/L, when used as an UWA on FF gear, not as a standard lens on crop.
Why do you say this? I use the 17-40 as a standard lens on crop and it performs very well for the most part IMO, as I understand it it's biggest weakness is used at the wide end without stopping down on FF. Using it on crop negates most of this issue.
The 17-40 is Canon's best full frame WA zoom.
I'm using a 17-40L on crop as a standard zoom because I plan (for CR regulars yes, really :-p) to upgrade to ff sometime and most of all the L is sturdy and sealed which makes a great difference because I regularly shoot in snow and dusty/dirty outdoor conditions. Just be sure to replace the lens hood with a 83J...
... however @f4 the 17-40L is clearly lacking in sharpness and except for the above reasons I really wouldn't recommend it on crop, even though it has a very good price nowadays esp. with Canon cashback rebates.
Canon 55-250/4-5.6 IS
Excellent little lens! I just sold mine because of disuse (but the 400D I used it on has been replaced with a Sony NEX).
Thirded. I can tell you from experience that this combination works. This is my go-to wedding setup: 17-55, 85/1.8 and two 550EXs. If you need more reach then get a 70-200/2.8 IS to complement the 17-55.In your place, I think I would go with the Canon 17-55mm f/2.8 IS. Personally, I think it is the best general purpose zoom lens for a crop body. It also works very well combined with a fast telephoto prime, such as the 85/1.8, which makes a very nice portrait lens on a crop body.You still need a fast enough shutter speed to get a nice and sharp photograph. My advice would be EF 85/1.8 USM, which is a fast focusing, sharp at 1.8, very affordable and overall decent lens for what you want it to do.In your case, I think a flash would be more helpful. You can then use your current lenses and drag the shutter. The flash will help freeze the subject while the longer exposure time will allow the background to be exposed properly.
I agree with these 3 suggestions. If this were me, I would start with a 17-55 2.8 and then add a 85 1.8 if I needed more reach. Adding a good speedlite or two is always a good idea as well and can be used to expand your creative possibilities beyond what you can do with just fast lenses and natural light.
The 16-50 F4L IS sounds REALLY intriguing, lets hope it's around 1k and I'll buy it.