Best purchase:
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This Boss RC-5 Loop Station. I scored this pristine condition looper a couple months ago from a wonderful guy I met on OLX. Couldn't bring myself to splurge on a new one and have been drooling over this for ages.
This is a guitar pedal that lets you loop and record over your playing, alongside drums. It also lets you record up to 13 hours, so you never lose an idea. Its as simple as you want it to be (as a basic one button looper pedal), but chock full of advanced features with a steep learning curve, with the ability to connect foot switches, MIDI controllers, if you want to go down that path as well.
The pedal is akin to having a strict teacher next to you giving you immediate critical feedback to your playing. You have no choice but to improve! I would encourage anyone passively playing electric guitar to look into getting any looper- there are many kinds.
I've been playing the guitar on and off for nearly 12 years, but due to non existent practice routines, I've stayed a beginner even after all this time. This thing has greatly boosted me picking up the guitar, playing and practicing for an hour a day (or sometimes more) for months straight. Inspired me enough to even start going for music lessons. I wish I had this many years ago! Its very cool that sometimes a piece of gear can vastly improve an otherwise stagnant hobby.
Worst purchase:
Fiio BTR15K
Not really a 'worst' purchase, but I've used it so few times (i still keep going for wired connection), that I'm kind of regretting it.