Aside from my new 245
Probably the best thing I ever bought was my lawsuit strat. 1980 Fernandes "revival" (62 copy)
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At the time I wasn't really up with the lawsuit stuff, but most people weren't (I must have owned it for 8 years now?). I was looking at a cheap fender - I usually shop at one particular store, it's a second-hand trading joint - but I wasn't really digging them considering the price. I tried an Ibanez lawsuit era strat copy that was interesting but pretty knackered (frets worn etc), and then I saw this. Same price as the fenders but my god the neck on it is incredible. It sounded pretty good, I could tell I would need to work on it, but the feel of the neck alone sold it. It has perfect fretwork, nicely rolled edges, nitro finish I suspect as it has largely worn off. The slab of rosewood is some of the nicest I have seen on a strat (can't tell from the photo).
It did have an off white guard ala 62 strat. I have since added a fender trem block, fender trem, the black guard of an older fender, new pots wiring switch etc, shielding, shielding plate under the guard, etc. It's now wired just with the first volume, and the tone pot nearest the jack works as a blend knob for the bridge pickup that is always on, so no matter your pickup combination you can blend in the bridge. Achieves convincing tele tones, I think, and allows all 3 pickups at once. The pickups are the factory ones... I had budgeted for duncans but after the trem block upgrade and new pots it sings.
Also a shout out to an Ibanez acoustic I bought for half price at a sale on a whim... I have played it every day for like 6 or 7 years. I have written a lot of music on it. It's my "grab and go" guitar for when I get home or want to practice etc.
As far as blunders go... my LP is a great axe but back in the day when I bought it I wasn't as fussy as I am now about fretwork. The frets are very low, like gibson fretless wonder low. It will need a refret soon and those are very expensive here, more than 50% the price of this axe in the first place. You live and learn.