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Which is the better investment. Depends :0
I sound like a stock broker don't I. You ask the question and I never give you a real answer!
So here's the deal.
Depending on what you need the container for, a different option may be the better route.
From the pictures above, you can see there is very little difference in the WWT (wind and watertight) shipping container and the Cargo Worthy (CW) shipping container in regard to the exterior.
Both have a crap load of rust, dings and dents.
They are ugly but they will keep your stuff secure (if you treat the rust!!!)
However, based on my experience buying both, the doors and the floors of the Cargo Worthy Shipping Container are typically in better shape the the WWT (wind and watertight) shipping containers.
Why does this matter, Oscar?
Because in my opinion if you are buying an asset or something you want for a long time, it may be worth the few hundred bucks for less hassle.
Screwy doors, replacing floors and fixing rust before it turns into a hole all take time, energy and effort.
My mentors have always stressed time is my best asset. Use it wisely. Its not fun messing around with a shipping container to fix all the things listed above, unless you are weird like me and actually enjoy that type of work.
So the long winded answer to my original questions.
Me personally, I buy Cargo Worthy from my vendors and even though they need the same time (roughly) in terms of investment to clean them up before painting, for a few hundred bucks they usually save me from having to deal with a few hundred dollars worth of issues in terms of messed up doors or floors (but save me a ton on time and effort).
I hope this helps.
Both the containers above ended up looking like the below. But it was a lot of manual labor.