There are more than a few variables, some that I'll be unable to adequately express, others that I'm unaware of, and still others that I don't have time for. Let's take OP's example since it's convenient.
I think it's one of two situations:
1. The candidate is a kid.
2. The candidate doesn't want to go to the States at a sub/conscious level.
I use 'the candidate', because OP might not be the person being talked about.
Let's look at it from a cultural perspective: Keep in mind that usually kids enter Med school straight from High school...from one insular community to another, with little room for personal growth. In many countries decisions about your life are not your own. If your father/mother says, 'Son, you're going to america, it's all been set up, you just have to pass this test'. The only way you can refuse is by sabotaging yourself. This might very well be such a case. It's easy to say,just say no. It's actually almost impossible to in that social dynamic (especially among the plebs). The reasons he might want to refuse are many, I'll just make one up - Say a marriage has been arranged, and the girl has agreed to marry him contingent on the fact that they go to the States, while he wants to marry some other girl his parents don't approve of. Again, this is just conjecture, but based on what he's said and his responses to me, he's clearly lying about almost everything, which is why I suspect that it's a family member writing on his behalf. Either that, or...he's a kid who didn't grow up and hasn't yet learned that people can help you better if you make them aware of your actual situation. There is so much more to add to the cultural perspective, but none of that is applicable here since I don't believe him.
To address what I disagree with in your post:
"It should take you 6 weeks and 1 attempt" - It should take you less if your education has been directed towards the test. However you look at it, Americans are being prepared carefully to pass each successive test...let's start with the SATs, where critical reasoning, vocabulary, and basic mathematics are assessed in MCQ format. Moving on, you see MCQs all through college and on the MCATs, the VR section stresses critical thinking once again. You learn HOW to answer vignette style MCQs in the sciences and you get your timing down. Finally, your shelf exams give you a solid foundation for the step. Even if you don't have shelves, all medical schools are motivated to address high yield material as it's financially beneficial to them in terms of reputation and alumni.
Compare this to exams elsewhere. Through all of school (as in from kindergarden to the 12th) and then medical school (directly, remember) there are usually a few simple mcqs, and mainly short answers and essays (the marking scheme is a pain to explain - involves assigned points and negative marking, but if you're really interested, lmk). This method of testing places a higher premium on memorization than understanding and reasoning. The mindset is...let the student learn the material first, and then we will teach them to apply it during internship and residency. This is just the first part of the exam - and I don't think I need to explain how woefully under-prepared a student is to answer Step 1 style qs after this pattern of preparation - I'll address the second part in the next paragraph.
"If you can't pass our boards, you're not on our level." - The second part of a medical exam (remember that this is medical school, and not residency) is called a viva, which is essentially an oral exam. This might sound easy, but it's more difficult than the written test in many ways. For the little tests, you have an internal examiner (a professor at your university) asking you questions with (usually) no supervision. They can ask you wtf ever they feel like and your answer needs to be tailored to the professor. I'll give you an example of a question. Say the Surgery resident during your rotation asks 'What is a sarcoma?', you might have to respond, "Sir, Baily and Love's define it as "A B C", Schwartz's Principles defines it as "D E F" and Sabiston's as "G H I"". Your answer might need to be verbatim in order to pass. Can you see how easy it is to fail an exam? This is why multiple retakes are commonplace in medical school. Because their exams are so very different, they are on a whole other level. One that is difficult to compare. There is another dimension to this. During accredition/standardized exams external examiners are brought in for the viva. These examiners tend to not be of the highest caliber since the best physicians don't need the money/can't be bothered to participate. To this, add religious/regional animosities. A punjabi might not like marathis, or a bengali might harbor dislike for tamils, or the person just might not like your face, not understand your accent, have not had a good cup of tea in the morning. On top of this you really don't know what they expect from you. It is so easy to fail.
"pretty hard to fail step 1" - is it any wonder that it isn't quite that hard to fail step 1? None of these apply to our dear candidate, since I don't believe him.