Atik 428EX: This was the first CCD I owned and it is a fantastic camera. The noise is extremely low, and I did not require darks while using this camera. The only negative is that the sensor is extremely small, limiting the field of view. For comparison, the fov of the 428EX @ 330mm focal length is comparable to a DSLR @ 800mm.
ZWO ASI1600MM Pro: This is the camera I am currently using. I was initially hesitant to buy a CMOS sensor, but am extremely glad I did. This camera is absolutely fantastic. The sensor is comparable to a dslr in size, and noise is comparable to the 428EX. Even with the low noise darks are still required to remove amp glow, but overall I couldn't be happier with this camera.
Atlas EQ-G: I have owned an Atlas EQ-G since 2013 and it remains my primary mount. I am mostly pleased with the way this mount has performed, although one drawback is the large amount of backlash in the gears. This periodically causes issues with getting a good calibration in PHD2, although for the most part the mount has given me little trouble.
William Optics GT71: I bought this to get a wider field of view. Optically the telescope is a high performer, although the R&P focuser is garbage. I plan on upgrading the focuser this winter.
AstroTech AT6RC: This scope is an absolute beast of a performer. It performs as well as my 8" Newt, but is much lighter on the mount.
Orion 8" F/3.9 Astrograph: This was my first imaging telescope and worked out quite well.
I have never owned a true observatory, but I have found ways to keep my gear setup outside and away from the elements. My first solution was a roll-away shed style observatory. This was built at my old house and worked very well for the two years it was in service. After I moved I contemplated building something similar but instead opted to try a Astro-Gizmo 365 cover. I was a little nervous about using the cover initially, but two years in I have no complaints. The only thing I have to be watchful for is hail, which I usually solve for by putting a large tupperware container over the mount and cover. I typically do not leave my OTAs or camera outside due to the heat and wind, but will on occasion.