Ignoring the "old vs. new" mostly, concentrating on Smartphone vs. digital camera (DSC):
Many people claiming that smartphones take "better" pictures than DSCs are not aware how much smartphones "cheat" (IMHO):
Those "photos" are very much interpretations of reality (by the phone), trying to guess what the "photographer" might want to see.
However it's amazing what nice photos these cameras get out from rather poor (small) sensors.
In contrast traditional DSCs take the shots you told them to take (showing all the wrong decisions you made).
So it may be more challenging to make "good" photos with a DSC, while it may be more challenging to make a smartphone take the shot you want.
Consider this example taken with a recent mid-class smartphone claiming "64 megapixels":
Here is the shot as you may perceive it in the display (I reduced saturation when shooting as the phone would over-do it):
It doesn't look too bad, but when viewing it pixel by pixel, the result is disappointing (note the large radius of "unsharp masking" specifically):
Finally a photo taken from a "real camera" (found in Internet, most likely full format like Canon EOS 5D), also pixel-by pixel:
You see the difference...
Finally on the financial aspect:
How long are you planning to use your smartphone, and how much does it cost?
Now if you want to spend only 200 USD, how much smartphone would you get for that?
It's your decision how much a good photo is worth for you.
I don't have an expensive DSC, only a "micro four thirds", where the body did "only" cost around 1000€, and my best lens did cost 1200€.
I also have a mid-class zoom that costs around 600€.
Still the combination probably is not as good as the example photo shown from in Internet (taken by a professional photographer).
I also have a really expensive mid-format film camera, but it does not make photos as crispy as the DSC while the lenses alone would cost around 4000 to 8000€ today (each).
But at the time when I had bought it, it was much better than the best digital cameras available.
Now when I compare the front lens of my medium-format wide angle lens, it's 110 millimeters, while my smartphone's wide-angle's front lens is about 10 millimeters.
Does size matter? I guess: Yes.
Obviously a lens with a diameter 10 times as large has 100 times the area (or amount of glass), so it'll be more expensive.
Meanwhile you may get better quality for less money, but there are still physical limits, so that larger (and more expensive) cameras and lenses will probably always better than the smaller ones.
But still the smaller ones could be "good enough" for you.
Also the weight and size of equipment may be important:
You can put your smartphone in the back of your trousers if you like, but maybe you would not like to carry a huge bag with equipment weighting 6kg or even more...
Finally: You may be able to sell parts of your traditional photo equipment when planning to "upgrade", but a smartphone after five years is basically worthless.