Two types of problems?

According to my experience, there are two types of problems:

Two types of problems

  1. For some problems I have been able to use some quick/dirty workarounds. Users are happy. Since the outcome quality has been acceptable for them.
  2. For some problems, no matter what I did with quick/dirty workarounds, I couldn’t reach an acceptable quality.

Am I right about my experience? Is there any software development topic about it. I want to know more.

If the above categorization is correct, how can I detect upfront, which category a problem belongs to?