Canon 6D - The 11 autofocus points clustered in the center of the viewfinder quickly seemed rather antiquated. The built in wifi was nice, as was the full frame image quality and ISO sensitivity. Still, the camera was slow, bulky, and rather uninspired in both design and feature set. This was my last DSLR before switching to Mirrorless. I don't miss it.
GoPro Hero 3 - It died suddenly with no prior signs of malfunction. I discovered it a few weeks before a trip as I went through my routine gear check. I tried a fresh battery, still nothing. I went online and found others were having the same problem. Turns out, it's so common that GoPro actually published a page of troubleshooting instructions. None of it worked.
Canon 40D - I had two of these and they were amazingly tough bodies made of magnesium alloy. I used them in horrific storms, frigid temperatures, and rain forests. The shutter did die on one of them and needed to be replaced. It shot 6 frames per second which was fast enough for birds in flight and sports. The downside was the LCDs poor resolution, and the lack of a tilt screen. This was my favorite DSLR.
Canon 10D - This was my first DSLR and it didn't disappoint. While it was only 6 megapixels and topped out at 3 frames per second, it was good enough to use for my first job as a photojournalist at Newsday. It's funny to reminisce about how I never dared to go above ISO 800. ISO 1600 was quite a noisy mess. We've sure come a long way!
Canon Elan 7 - I shot slide film with this beauty and loved how quiet and stealthy it was. If I recall correctly, it didn't have a spot meter so I had to use the partial meter. It was a joy to use though, and the unforgiving nature of slide film forced me to really master in-camera exposure.
Canon Rebel (Grey Market) - Yes, my very first film SLR, and the camera store pulled a bait and switch. They showed me the silver USA model and then switched it out with the all black grey market model. I didn't know better and went with it. When I tried to pay with a credit card, the salesperson repeated, "No, no, show me the green!" Despite all of this, I loved the set up and used it extensively to start learning exposure and composition.
Other stuff worth eulogizing:
Canon 17-40 f4, Canon 70-200mm f2. 8, Canon 100mm f2.8 macro, and the Canon 400mm f5.6. While all of this glass was truly high quality, it also weighed 25-30 pounds. Long hikes up and down mountains would become painful and grueling after just a few hours.
ISO 50 Fuji Velvia slide film - seeing an image for the first time on a lightbox through a loupe was exciting. This film was vibrant and virtually grain free making it a lot of fun to work with. Many image editing software companies have tried to recreate this look ever since.
Adobe Photoshop - it's true, I haven't needed to use Photoshop in years. If I can't edit it in Lightroom then I've done something seriously wrong.