...Yes this is the age old question of multiple less expensive guitars or one more expensive guitar. In this case the hypothetical question is referring to a single purchase rather than your only guitar but I want to know the why. In my case I’d go with the core route, I reversed this process (sold a core for several less expensive guitars and am still kicking myself years later).
There was a time when I was younger and had greater wealth, and owned several high-end PS guitars, perhaps one at a time, with one other core model and an acoustic.
Because life often throws you a curve and you can't justify owning such expensive gear because your chops aren't up to snuff, and it seems like you're overcompensating, you choose to downsize your expensive gear and seek out more cost-effective gear that satisfies your needs yet still feels comfortable and easy to play. It becomes a wash, and whether you warm up in your relationship with your guitar or not, will determine whether you face potential "disaster" or not.
As for me, I sit her with a warm cuppa tea, realistic in my expectations. My current guitars are seen in my sig line, only 3, yet these 3 cover all of my current needs for guitar practice and potentially live performance once it will be possible to do so again.
While many "want" luxury, wealth is elusive and deceiving. Many people have sought wealth only to experience job stress and family strife. The truth is, the 2 most common reasons for family disagreements is: sex and money. If one is content with what they own, or can get by with owning fewer material possessions, perhaps they might be happier because they are not as fettered by the "want" many people commonly experience.
Yes, this is contrarian thinking towards supporting guitar builders and business in general. If perhaps you might recall, your parents and previous generations had to get by with much less and had to save for important things that were expensive, like food, shelter, or clothing. As time progressed, the standard of living rose, and the cost of prohibit expensive things became more affordable. Banks offered loans that you could pay back over time, some stores offered layaway payment plans.
Yet, people still could not see the reason for why saving money for important things was necessary. They soon discovered that if they rode high and lived lavish lifestyles, they soon discovered that wealth was fleeting, and they either lost their money to whatever vices they had, whatever ills that faced them. This was the history of Americans prior to WWII. Even today there is an inordinate outcry because of the disparity between the wealthy and poor, and much of society's ills today are caused by poverty.
Yet, with all of this occurring in real life, and with many people trying to live despite the pressures of others who urge us on to buying more, we might ask, when will we learn that "want" may lead to temporary enjoyment and pleasure, but realize that the pleasure of owning something of high value is still temporary. Until you get you next "gear fix," we all are woefully addicted to buying and selling, in order to feed our habit.
That being said, many may consider this a blemish on people's viewpoints. I do not fear the reactions of others, but only wish that they realize how foolish they might be. This is not a bad joke, it's very real. Your parents knew better; your grandparents even more so. We live in privileged times, and many fight over money, position, and power, all for self-promotion, and being able to boast about their triumphs. Where have we gone wrong?