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Yes, although things have been getting better, slowly.
I've found that the most effective solution for our organization is to build credibility by accurately forecasting the impact of failures. I don't mean apocalypse-level warnings, but simple facts like "if this server goes down, these are the services and number of customers (internal or external) that will be affected, and this is how long it would take (estimated) to go through the process of bringing a new server up."
I think most people on the decision (money) side can make logical decisions when it's presented in terms they understand. That doesn't mean they will always say yes, but at least you've educated them as to the risks.
We do, but we also have a program to identify and remediate them. As branfarm stated, its mostly about presentation. "We need $100K to replace old servers" is far less likely to win approval than "We need $100K to keep applications A, B and C running because the hardware they are on is no longer supported by the manufacturer and a failure would mean ...". Same for network infrastructure. You have to sell the upgrade not much differently than if you were selling something to an external customer. The money may not always be there, but you have performed your due diligence in making the proper notification. It doesn't change your response when the old gear gives up the ghost, but at least you cannot be accused of ignorance of the problem or failure to raise the issue.
As hard as we try, we still have two or three things running on stuff that is past end of life... We sound the alarm about these at EVERY opportunity. Only thing you can do is point out the potential costs, and try to get things moving. Sometimes it's not money, but time to get to it!