We shouldn't but this is the democratic system we live in. Voting happens at the ballot box, in the ledership races, in party fundraising, in union organizing, in the courts, in ad spending.. Turns out dollars are votes too and some have more of them than others. If curbing our rights is profitble for some with more cash, or sometimes just desirable, we'll have to raise our dollar votes against them. And if we're lucky, our ballot box votes might have made it cheaper. Never free. It's super fucking annoying and it's too much work. Improvements are possible but that's where we are today.
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Only if you can afford it. There are plenty of people who cycle and can afford it and they should contribute more. I contributed a chunk.