As an admitted non effects user, I have a couple of questions. Why do I see so many pedal boards with multiple 'Fuzz', 'Distortion', and 'Overdrive' pedals? What is the difference between the three?
If one of those little short connector cables or a jack in one of the pedals goes bad on stage, how long does it take to find it and get your signal back?
There are a LOT of different descriptives people use for the differences between the three, and some of them can overlap into the others. It can be a fine/confusing line between the three. On a very basic general level (and this is just my understanding/experience... yours may vary):
Overdrive can be used to put just a little "grit" or "dirt" or "hair" on your tone. I believe overdrive pedals were originally designed to emulate the sound of a tube amp when it breaks up, so you can get that sound at low volumes. Some overdrives are low- to medium-gain, others are medium- to high- gain (which is where it may overlap into one of the other categories and cause confusion).
Distortion is more aggressive, getting "crunchier" than overdrive.
Fuzz is generally the most aggressive of the three effects. Fuzz can still be used in a “barely there” manner, but I'd describe the effect more as "loud, mean and angry." lol Lots of people around TB love their fuzz, but I’m personally not a fuzz guy myself.
As far as having multiple "dirt" pedals on a board, it's because they can all have distinctly different flavors, even from overdrive to overdrive. My current secondary board is below and somehow ended up all overdrive and envelope (with a token octaver lol)... The Darkglass B3k is more transparent, the BlueTube has an actual tube in it and a 3-band EQ (“warmest” sounding overdrive I’ve ever played!), the Flipster is a copy of the preamp circuit from an Ampeg SB-12 (so it sounds like an Ampeg SB-12 lol) and all the Sansamps have their own thing going on, like a combination of tube/cabinet emulation... tough to describe exactly.
Probably the best advice if you’re interested is to start with a multi-effect pedal. That way you can experiment with different effects and see what you like. Also, listen to as many clips of pedals as you can find or recordings by your favorite artists and then try and track down what gear they use.
As for hunting down pedalboard problems... Yeah it can be a pain in the a$$, but generally, cables and such don’t move much once you get your board put together, so you’re more likely to have & find a problem
right away, rather than down the line. I'm
constantly messing with my board and I haven't had a cable go bad yet. *knock on wood* Anytime I have a problem, it's usually user error. A pedal I forgot to hook power to, or didn't get a jack pushed in all the way...

lol
Hope that helps!
5sg.