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You might want to broaden your thinking unless what a nicer instrument might offer means nothing to you, in which case buy a lower end instrument.
Yes, new basses can depreciate. The cool thing is that you can also buy them after they do that. That doesn't seem to be factored into your question.

Would you rather own 4 used Kias or one new Toyota?
I guess my misunderstood point was what's the point of owning many lesser items than one good item. Maybe I should have referenced owning four 2003 Kia Rios and one nice new Kia ,(all garbage IMHO). No wonder I stopped posting on this site. Time to crawl back in the woodwork when the analogies get criticized.Not really a good analogy imo. Kia makes some pretty decent cars now and their cheapest is about the same price as toyota's cheapest. A better analogy would be would you rather 4 used toyotas or 1 new lexus. Since they're the same company, it's more akin to the Fender/Squier relationship.
And to the OP. I don't often plan on flipping my basses, so resale value doesn't come into play much. If I see a bass I like, I buy it. If there ever comes a time where I don't want it anymore, I sell it. Any difference in price between what I bought it for and what I sold it for, I consider it the cost of my lease on the bass, much like leasing a car would be. If you're that worried about depreciation, buy used. There will be a much smaller loss.
Being on the lookout for new gear and noticing how quickly high end gear on average looses its value second hand, would it not make more sense to just buy a good low end one every x years?
For example high end Fender Professional / Elite loose about 10-15% first 3 years. Then slowly decreasing and only if in good shape.
For that kind of money I could get me like about 4 good Squiers or nearly new Standard/Player....
Knowing yes that the premium ones have that (little) quality extra.
It remains to be seen if within 20 or 30 years, todays gear will be treasured as much as original 60s/70s gear is today?
There is some price point at which you can get a bass that functionally does everything you want it to do. Beyond that, you are paying for fancy wood, inlay, fancy finishes or a certain name on the headstock. You can argue about exactly what that price point is. I don't think it is any higher than $1500 and is probably less than $1000.
That said, I have a bunch of basses, four string, five string, fretted, fretless, and eight string. But I play my #1 bass 90% of the time. That bass is a G&L L-1000 that I've been playing since I bought it new some time in the nineties. I have no quarrels with it.
10-15%? The typical bass loses 30-40% the instant you use it one time.Being on the lookout for new gear and noticing how quickly high end gear on average looses its value second hand, would it not make more sense to just buy a good low end one every x years?
For example high end Fender Professional / Elite loose about 10-15% first 3 years. Then slowly decreasing and only if in good shape.
For that kind of money I could get me like about 4 good Squiers or nearly new Standard/Player....
Knowing yes that the premium ones have that (little) quality extra.
It remains to be seen if within 20 or 30 years, todays gear will be treasured as much as original 60s/70s gear is today?