Time/Process of Hooking up New Equipment

I feel as you do.  I tend to put off making changes because I know, once I start, there is a long list of "Oh, dang, I could do this!"  or "Whoa! Why didn't I think of doing that?"  and of course, the ever present, "It would be a lot better if I wire it this way..." and "What was I thinking when I wired it this way?"

Yep.  Been there.

Changing equipment always opens up a new can of worms. There will be more work to do. Taking your time is a good thing, no need to rush. It takes time to evaluate. 

Yeah, I wait until I am not rushed. That reduces the chance of stupid mistakes.

With new gear I ensure that I have the time and space to get it set up. I also try not to come to any immediate conclusions and let gear burn in for 1-2 weeks before starting to tinker with positioning or different cables. Even after burn in, it takes some time for the ear to get used to differences, so patience is surely a virtue. 

Whenever I think it can be most easily slipped into the rack without being noticed, if you know what I mean ......