Believe me, no equipment is ideal and getting to know that takes some time.
What I often do to learn my gear is to limit number of extra gear (mainly lenses) I'm taking with me. Although I own quite a few lenses and this collection seems to grow over time, I hardly ever have more than 2 with me. This way I limit my choices. I don't have to waste time wondering whether I should take a photo with prime or zoom or maybe telezoom. I just take it. I also try to change my setup from time to time. What I mean that one time I will take a wide-angle zoom lens + telezoom lens but the other time I will take wide-angle prime + standard zoom lens. What I try to avoid is to take 2 lenses with same or similar focal range. Instead I try to take lenses that would allow me to cover wider focal range.
When I'm back at home and download my photos I can clearly see issues and strengths in each of the lenses. Of course I don't inspect photos at 100%, trying to calculate lens' resolution for instance. No, there are many great tests which do it in a much more reliable way than I could do at home. However, looking with some care I can quickly see if there is strong colour fringing (chromatic aberration), vignetting or too strong distortion.
After some time you will know your gear perfectly. For instance now I know that for any night/sunrise/sunset landscape photos 24 f/1.4 II lens is a perfect choice. Low chromatic aberration and low flares help significantly during sunrises when I have sun in the frame. However, my general travel lens is Canon 24-105 f/4 L. Although it has some problems with chromatic aberration and isn't that sharp it's a great general purpose lens offering very universal range of focal ranges. Similarly if I'm to shoot some action I will probably use Canon 50D. Its fast burst (6 fps) mode is a great help. In addition the fact that it's a crop body it will make each lens longer (eg. 100 mm on a crop body becomes 160 mm) what is also very useful for action shots. However, for any serious landscape photo shoot or any night photos I'm taking 5D MK II because it offers lower noise and in general better image quality.