So, this is actually a complicated question.
Two people who eat the same amount, we'll say 2,500 calories a day to insure no malnutrition, have a similar muscle mass to bone mass ratio, and are both similar in hormone palette, then yes. The skinnier of the two will likely struggle to gain weight compared to the bigger one.
This is mostly due to having more fat cells = easier to get fatter. But having all these things be lined up would be absolutely unheard of, so it is better to think of "harder" or "easier" as relative to the amount of effort a person puts into the task.
The unfortunate truth is that analysing one's gaining is a very math and monitoring-heavy process. So if you aren't able to just constantly stuff yourself it may be difficult to figure out what specifically plateaus someone.
Many people start skinny, though, ans get rather large.
5 days