I kinda agree with both of you. Given how big CR is (or at least used to be) their site could be much better. Watching anime for free will in the end always be at the cost of anime producers. That being said, if you want to watch anime in English outside the US, it can be pretty pricey. Many of the titles are not even released because of some licensing issue. If I access CR for example, I only see a fraction of the titles someone from the US gets shown, they don't even appear on the anime titles list.
And if you want to actually own them, we are often talking about 60-70 dollars per season with only a single language, no subtitles or other languages such as English (not even the original Japanese dub in most cases, even for the Ghibli movies).
So I'd say if you actually have the money, you should definitely pay for as much of the anime you consume, for moral reasons as well as simply for practical reasons such as pumping money into the anime industry. If you don't have the money, you are often either left with not watching any anime or watching it illegally. That being said, getting a subscription at CR for example is around 10 bucks a month, so even if you only get a fraction of what others get to see, it might be a great compromise of paying as much as you can and watching what they offer, and either not watching the rest or illegally streaming it.