You should get this thought out of your headā¦
How good do you think you need to be?
Itās not really about expense, itās about quality.
We arenāt just learning to play guitar - weāre learning to play music. Okay, so playing music well depends hugely on our ability, but it also depends on the quality of our guitars.
All of us deserve the best quality guitar we can afford.
Ah you mean Lucy
As a lefty, I donāt have soo much cohice and it bothered me that the cool Jag shape and 24" scale always had to be the same thing over and over again.
A fellow lefty and most of all hobby builder took my design and made it happen. He did some useful suggestions on some details and damn do I love how she looks, feels, plays and sounds! Pickups were custom made by him as well so the bridge is excellent for fingerpick/strum mix style. The red is the red of the Soviet Union flag 
Journey
I loved the whole journey of this. This existed only in my dreams for years but bit by bit, it came to life. The process with the builder, mixing and matching the specifics, seeying your dream take for in pictures he sended me.
Because of the love and the specs, it facilitates my playing, my style and my inspiration.
ā¦but itās not that I was at my guitar peak when I ordered it
I saved some specific money for it, selling other gear, doing a bit of side hustle. It was a dedicated fund and it took me a while but it felt totally justified!
Live in action:
I only have two guitars - a Fender Strat and a Martin acoustic. I saved up for each of them.
While I was saving, I played several guitars at my local shops to figure out what I wanted. And, when I had enough money, I bought with the intention of having them for the rest of my life.
Iāve had my electric for 5 years and my acoustic for almost 3 and I have no desire for another guitar. I play both of them nearly every single day and I still get excited every time I pick them up. I never wonder if I should have gotten a better or different guitar. I never wonder if my guitars are properly set up or if they could play better. I never wonder if my guitars are holding me back. Almost every day I hear something in them that make me go āwowā.
So, I would say I am definitely in the āwaiting for good guitarsā group, but Iām not really in the market anymore.
Great thread JK, Iāve enjoyed reading every post!
Iām going to add my thoughts in roughly chronological sequence since my thinking has changed as my playing skills, time commitment and satisfaction with my progress increased.
I started off with a $200 Squier bullet Strat from Amazon. It was hard to play, improved with a setup and worked well in my early days and is now drop tuned for occasional slide guitar practice. I also had a $250 Washburn folk acoustic that had a high action, but was good enough for BG1/2 finger style lessons but made the F chord harder than it could have been on a better starter guitar.
I turned the Washburn into my luthier training workbench and experimented with incremental upgrades to see if I could hear and feel the difference and in some cases, did I āstop seeingā the difference. Gotoh tuners were significantly better at staying in tune, easier to āfine tuneā due I assume to the higher gear ratio, and looked nicer but I donāt notice that any more. Ebony pins with faux abalone dots still look nicer and changed the tone slightly, etc. Each change did make a difference.
My first upgrade was to a $500 Yamaha that I soured on quickly. It wasnāt a big step up in playability, looks and tone and I donated it to a local charity.
My second upgrade was to a Fender American Pro Strat. It was and still is a big step up from the Squier - I love how it looks, feels and sounds. I didnāt try a MIM strat or something in between - I wanted the name and waited till I had the cash. I would play it more often if it werenāt for the inspired by Gibson ES-335 I bought last year. The shorter scale is easier to bend, the humbuckers added to the tonal palette, and for the price, for me, this was good value for money relative to even the lowest priced Gibson. So perhaps a MIM Strat wouldāve been fine too but the heart wants what the heart wants. 
Which brings me to my Martin MD 000-28. Iāve wanted one ever since I watched EC unplugged live on MTV back in the day. Iāve spent hours learning the history of the brand and hearing my favorite artists rave about the guitars and play on them. It took a lot more saving up, but Iām very happy with it. I love how it looks, feels, plays and sounds and am blessed I could get one. 
I also have a Cordoba fusion nylon string which was closer to the $900 mark, and itās also a lot of fun, different sounds, feel etc. I liked it a lot more than cheaper nylon strings and I didnāt think more expensive ones were materially better sounding or playing, although there is more visible craftsmanship and pretty inlays etc. in them.
I wish I knew more than two classical songs but itās also fun for any song done finger style.
In conclusion, buy guitars that broaden the variety in your collection, be sensitive to diminishing returns, unless itās for a brand or model you really desire, then save up and go for it. 
6 posts were split to a new topic: Improving tone . . . new guitar or swap pickups
Thanks everyone for the great discussion on this topic.
I have considered it! Something about PRSās doesnāt quite grab me, though. I get why people like them, though.
I agree with that @Kasper, up to a point. On Fenders the component upgrades from Player ā Plus ā Am, etc etc to Ultra are pretty clear. On the Gibson side? Seems like often you can get all the tech on an Epiphone, but if you want a Gibson, youāre paying for the name. But I guess thatās also true with bikes as well - an italian brand vs a Giant, Trek or Canyon.
For me, itās that I can get something different enough for my purposes without paying custom money.
I was being a bit self deprecating there, but really in jest, Iām not the type to beat myself up. Iād be pretty happy with something flash, whether Iād want to pay for it is something else entirely!
I love your Jag. And I know what you mean about Jags always being the same thing. Same/similar bridges [edit: typos]. Some kind of wood burst. Often the same pickups. Iād love a dual humbucker 24" scale Jag in a solid colourā¦ theyāre around, but rare and used only around these parts.
I have too - and enjoyed reading your post Ashu! Shows how we learn what we like and donāt like as we play more and try different guitars. I think thereās something to getting nicer guitars as you get more experience.
And with all thatā¦ itās helped me make my mind up. I decided I definitely wanted something different in scale length to what Iāve got, and something midrange, which would do it for me.
So I went and tested one of the guitars Iāve had my eye on for a while at a music shop about half an hour away from here, and I ended up putting a deposit on it.
I should pick it sometime in the next week or so.
Oooh what did you get?! 
Just caught up with this thread, great read.
But now you are just teasing.
Iāll save that for the NGD thread when I get the guitar
I have a few top-tier guitars, some mid-range guitars, and a few entry-level guitars.
I find that the quality of the instrument tracks with price often, but not always. I also find that price and quality track better with acoustic guitars. That is, when you buy a quality, expensive acoustic itās usually worth the extra money. When buying an electric guitar higher price is not as reliable an indicator of quality (especially these days). My favorite acoustics tend to be the more expensive instruments. My favorite electrics are all over the price range, including one thatās a Squire.
In general, my advice is to get the best instruments you can afford. āBestā is subjective, of course. Also, if you want a certain brand because of the brand, then go ahead and get that brand. Get instruments that ā for whatever personal reasons ā make you smile when you see them, pick them up, and play them. Life is short; play guitars that bring you joy.
So Iāve got 10 guitars. Only a few are important. Ones I no longer have got away, damn it.
#1A cheap 1986 Alvarez that I love and more because I learned on it to play and I learned on it to tweak and maintain. #2 A 1977 Gibson LesPaul Standard I traded for with $500 as the trade value. Itās a player at 9 lbs 13 oz, and all original except for the bridge pup is a Dimarzio, which everyone did in '77. #3 A MIK Epi Special from 1995 which is a beast on stage, light, and just wonderful. I paid $32.18 cash for it in 2007. I put some hand work to its frets and set it up. #4 A Squier Strat, maybe 2012, Indo and Sunburst I bought at auction thru Goodwill. Once again I took the micromesh to the frets and eventually found a fun fretboard. Nice light player with classic Strat sound. Oh and I guess #5 a Martin D15-M 2012, it sounds nice. Plus some others I could go on.
Whatās important is not what you pay or play. Itās what you learn to play. Itās what you enjoy. Itās what you learn to fix and maintain as your favorite axe changes over time and through the weather.
I love guitar. No matter what you buy next, you know there is an older one you could pull out a play ever more so sweetā¦_R
