It's quite a complicated topic based on multiple factors.
Let's begin with getting into a new director. Let's say you don't know anything about the man, only that he's highly acclaimed and hyped all around, because this is the main reason many people would like to discover his works. Of course, when you get deeper into it, you will discover new filmmakers on your own and sheer interest will lead you to their works, but we are just starting here, alright? Now, when there's a director and I haven't seen any film he made I would most of the time just go for his film that has the highest rating (more often), or just for a film I stumbled across (not that often, but happens). So, for Kubrick I'd like to either go for 2001: A Space Odyssey (because it's got the highest rating), or for The Killing, because this is the first film of his I came across surfing the Net and it got me interested. Another cool thing to do, when you have seen at least two films of a filmmaker and you love them both, is to watch all his works chronologically. Not only can you see his style developing and skills getting better (or worse; depending on the director), but you also start to perceive things you wouldn't the other way. Like, some actors that starred in more than one film of his, them getting older, different approaches, variety of interesting performances. It gives you a broader look on the works of a director.
Why do people hate a director at first, but after some time get to love him? There can be a lot of reasons, but I came up with two most apparent. The first one, quite obvious, is that your tastes change. Some things we've disliked back then, we're keen on today etc. All in all, people change and so do their tastes. The other reason for this is a so-called development of a taste. When you get into something it's hard to omit the basics and immediately get to the more advanced stuff. Nobody starts learning English from Past Perfect Continuous. Everybody starts from Present Simple. Maybe it's not the best comparison there is, but I hope you catch my drift. So, if you're interested in cinema and want to develop your tastes, you will get deeper and deeper into the world of cinema. GRADUALLY. Of course, you can go for the most hardcore arthouse film there is just after you've finished Transformers, but the probability you're gonna love it is very low. Now, if you take little steps and gradually go from mainstream, conventional cinema, through a less-conventional, more arthouse, through arthouse, experimental and so on you will eventually find out you came from contemporary comedy to Dada, from modern blockbusters to Brakhage-like abstractionism, from Cameron and Bay to Bergman and Tarkovsky and from Hollywood classics to Kirsanoff's visual poems. You can stay at any level as long as you like, it's still okay to like the more popular, mainstream, less obscure, less 'refined' stuff. It's alright to dislike some films, maybe even whole movements. You don't have to love everything, but you have to be interested in new possibilities. You have to seek new experiences. Want to develop yourself, because if you stay at level 1 and think Michael Bay is the best director ever you will most likely find Bergman boring and pretentious.
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Look, I'm not judging you - after all, I'm posting here myself, but maybe, just maybe, if you spent less time here and more time watching films, maybe, and I stress, maybe your taste would be of some value. Just a thought, ya know.
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