I've reconfigured twice. Both times it was a major PIA. Both times I was really glad I'd done it.
The first time it all began when I simply switched from a USB to a Firewire interface.
The FW cable was too short, and when I tried a longer one the interface freaked out. Only solution was to move the rack and computer closer together. I figured if I was going to be shuffling stuff around I might as well move the desk into a better location, for acoustical reasons. But that meant moving the vocal booth next to a window, so I had to cover the window with 703. Now the room was too dark, so I added floor lamps. Not wanting to run the (flourescent) lights on the same circuit with the audio stuff, I built a separate distribution box. I also built speaker stands because the speakers had previously sat on a shelf that had to be torn out for the new configuration.
It all took over a week to accomplish. Only after it was done I realized that the only spot I could put the subwoofer in was the absolute worst place for it. An entirely new configuration would be required. Later, we sold our boat and freed up a garage, so I moved into the garage and applied all the hard-earned lessons - starting with where the sub would go.
But you gotta do it, you know you do. Not just for convenience and acoustics, but also for the dust bunnies that gather in places you never look in.
My #1 tip: velcro. Color-coded velcro ties are handy, but I'm cheap. In the garden department of your home-improvement store, you can buy this paper tape that sticks to itself like velcro. It's made for tying up tomato plants. It's cheap, can be cut to length and re-used. Great for tidying up cables.
For large bundles, there's plastic conduit that's also inexpensive. I ran all my synth cables in them, so when I pack up the synths to take to a gig, all the studio cables remain neatly on the floor, ready to be quickly reconnected later. Colored electrical tape identifies left versus right audio and in versus out MIDI.
Also, using conduit makes it easier to keep power and signal cables separated.