This is exactly what your school should be teaching you. This is literally the crux of practicing medicine - people come in with stories and you have to figure out what’s going on. Are you at a US medical school?
In a nutshell, my standardized test approach is to read the last sentence of a question first and then skim the answer choices. I do this to know what kind of question it is - diagnosis, next step, random factoid, etc - and then the answers broadly tell me the scope and subject area (ie. if I see five diffferent heart conditions I know what system I’m looking at, or if I see a mix of heart and lung and renal then I know my job is to distinguish them).
For a diagnosis question you are looking for clues. Already from your prompt I know it’s a 26 year old male so I’ve excluded all GYN problems and most diseases of older adults. This question is most likely going to be looking for an acute infectious issue, surgical issue (appy, Chole, hernia, torsion), trauma, or congenital issue of some sort. The answer choices would quickly narrow down what I’m looking for.
If it’s a trauma then they have to give you enough info to distinguish the different injuries listed. They can give you an X-ray, physical exam findings, and of course the history for mechanism of injury can all help point you toward the answer. It’ll be descriptions of various tests and you’ll have to understand the anatomy and exam well enough to figure out which thing is broken or torn.
Step 1 is much more focused on your knowledge of basic sciences so the trauma question may actually be designed to test your knowledge of upper extremity anatomy. The infectious one may be looking to test your understanding of the microbiology of common pathogens. Regardless, it’s still a matter of you looking for clues and ruling things in or out.