Before the www days, information wasn't widely nor promptly available and we were left to know only what we read about in mags or music store catalogues.
So, and although in retrospective it can be seen as a good, educational thing, much about good gear discovery was a matter of blind, expensive and often frustrating trial and error...
For example, for a very long time I fancied a multi-effects unit. At the dawn of such things I promptly started saving to buy a Korg AX1-G, only to later discover that the footswitch travel was way too short, no pre-selection of patches could be made (you'd have to scroll up or down the entire bank) and the display was not backlit. This rendered it useless for stage use.
Then I started reading in magazines that amp simulation was the thing to go after. It wasn't long until managed to get a Digitech RP100. Sturdy construction, the effects editing was a breeze, the visibility was great, it featured an expression pedal interface. All was good for a few days but then:
The power adapter was an awkward AC output thing very difficult to replace, battery consumption was unacceptable and, most importantly, the bypass sound was quite literally useless crap. You'd have to program a "clean" setting to have some sort of clean and unaltered sound available.
To make a long story short, I've spent quite a decent amount on playing and recording gear but this first post of the year (and last year's most precious gear award) goes to the single piece of equipment I crave the most (other than guitars and amps themselves): A looper pedal.
Nothing contributes more to what guitar playing is all about for me: Self enjoyment, self entertainment and creative expression.