Holy smokes! 40!
I can go from 7.26.0-1+wheezy10 to 7.26.0-1+wheezy11, and such...
Should I? How? Is it going to crash everything?

No reason to think why it should be a problem.

If you want to review a specific package and the reason it was updated you can look at https://lists.debian.org/debian-stable-announce/ or https://lists.debian.org/debian-security-announce/ as applicable.

No reason why updating would be a problem or not updating?
Also how do i update? Is there a one click way through linode dashdoard or is it a more involved process? Thanks

Debian distributes updates in order to fix bugs. The updated packages are given careful testing.

If you choose not to install updates, you are choosing to keep known, certain software bugs to avoid the tiny chance that the update contains a new bug which will cause a problem for you. This is generally not a smart idea.

Review the Linode Getting Started guide for instruction on installing updates.

But presumably something told you that 40 updates are available; didn't it offer to install them for you?