How do you handle updates?

I am working on my sites for a long time, because I got an imagination about how it should work and spend a lot of time and money into it. But this often needs a lot of customizations which is the point of my thread. How do you manage your customizations in relation to updates? I am always happy to see new blog posts on the Stackideas page about updates and upcoming features but in the same time I feel like getting overwhelmed, because of not getting it done.

My workflow looks more or less like this:
Customizations -> new updates -> make old customizations work for the update -> new customizations -> new update -> make old and new customizations work -> and so on. There is nearly no time left to generate any content.

Am I the only one staying for a version a very long time or do you prevent any customizations to stay update-able? I have to admit that I lost my enthusiasm due to this more or less. I just asked myself if it would be better to keep my customizations and stay without updates for a while or better get rid of the customizations and go on with easy updates. Would be great to read some experiences from other guys like you.