Started off with $8 china guitar that I borrowed from cousin with action 2 cm high on the 12th fret. Practised by chord work until my fingers literally bled since the strings were rusty and I didn't know where to buy new strings or how to change them.
2nd guitar was an Epiphone acoustic with Shadow piezo. Learnt strumming patterns, soloes and riffs on it.
3rd was a fake $80 Fender replica I carried back from china. Learnt more about electrics from it. Mastered barre chords on it too since my fingers weren't strong enough to do proper barre chords without any unintentional muting on the acoustic.
4th was a Crafter Convoy sp. One guitar that feels dead and lifeless compared to my PRS, but the amplified sound is to die for.
5th was my PRS. Worked in Cold Storage Parkway over my sec 4 holidays, which were the only holidays I could enjoy not being bogged down by schoolwork. Earned around $1.5k, + my life savings of Chinese New Year ang baos which I have never touched before, managed to buy the PRS with my own money. It helped when I showed my mom the guitar cause she was very impressed by it since it just looked right - colour, shape and all, especially the birdie inlays (except the price tag =D).
And there! I owned a PRS when I was 16 years old. It is very possible to get high end gear at a young age, but you got to work really hard for it. Sacrifices sacrifices and sacrifices!