When I was a kid, most of us were lucky to have a beginner guitar. In my case, I wore out the original bridge and two sets of tuning keys on mine before I got a professional instrument.
But, several have asked me how many instruments do you need?
Professionals often have several guitars they are comfortable to use as backup and to address the needs of the different styles of music they play. For example, a "classic rock" player might have two Gibson Les Pauls and one Fender Stratocaster along with an acoustic guitar or two.
If you're a hobbyist or play in a "tribute" band, perhaps what you need is an instrument, amps, and effects similar to your idol or just ones that captures your fancy. Just remember, that buying an instrument like your idol won't automatically make you sound like him. Beyond talent and playing technique, I find other things including body mass can influence your sound.
If you're a collector, then you need to buy what you like of course, but be mindful of which instruments are likely to gain in value over the time you plan to own them. I suspect that most of the instruments popular with "baby boomers" are already about maxed out in value. I'd target a Jackson Randy Rhodes and early Paul Reed Smith guitars. Just remember, they all need to be maintained, kept in a controlled and secure environment, and played.
If you're an artist yourself, it important to be hip to the classic tools of the trade as well as the latest things, but you might find that a mixture of products best addresses your needs as your goal is to sound like you and not the Rolling Stones. One thing I've found is that experienced players tend to look for certain things in "their sound", so they often sound "like themselves" even on instruments that don't belong to them and could be of marginal quality.