Hey Joshy! Coming from a small island nation, where I'm assuming the weather doesn't vary all that much from the north to the south, the US can be a bit of a shock. When picking a place to live in the US, weather must be a strong consideration because every region of the US has such different weather. So it really all depends on what your comfort level is.
For example, I live in Rochester, in upstate New York. Summers here are fabulous but rather short. Winter comes in October and doesn't leave until April and usually dumps about 10 feet of snow on us at least during that time. We've even had snow in May and September before! XP
Once you start to go south though, it changes fast. By the time you get to Virginia, winters are down to a month or two and very little snow. Florida, there is no such thing as winter. (For those who live in the south, no, 60 degrees does NOT count as winter weather :P).
It changes further going east to west. The east is cooler, more forested and mountainous. The midwest is flat and humid, the southwest is dry and hot, and the northwest is wet and cold.