First of all, I feel your pain. I really do. We’ve passed that on, because it's great feedback. I know my friends on the teams that work on these problems are aware of it; it's just more complex than I wish it was.
Paraphrasing what I hear from colleagues: The reality is that our stations sit on NYC streets for many, many years. We've come a long way in designing our hardware to be incredibly resilient to the challenges that the streets pose; plus, we have hard-working maintenance crews out there every day to make them work. But, things still go wrong (and we’re working hard to shrink that list). What could possibly go wrong, you may ask? The list would amaze you – skyscrapers blocking the sun from reaching our solar panels, trucks backing into our kiosks, even rats chewing through electric cables. (What, they got tired of pizza?)
One of the things I've learned as a Bike Angel is "if something looks too good to be true, it probably is." Just one example: one afternoon I saw a 12-point pickup station in Union Square, surrounded by 6- to 12-point dropoff stations. I ran to the subway, got down there as fast as I could and... none of the bikes were releasing. That's why there was one pickup station surrounded by dropoff stations. I used a few words that would be unprofessional to share here (and I'm guessing you've used some of those words yourself). Worse yet: this wasn't the first time it had happened to me.
I keep falling into that same trap: "look at all those pickup points, surrounded by miles of drop-off stations!" I'm slowly learning to switch to the Parking view, and to check a few times. If there are zero parking spots, and it stays that way for 30 minutes, it's probably a station not releasing bikes. I realize that isn't a long-term fix, and like I said, we’ll pass along the feedback.