I agree with what Dave said, mostly.
The excellent documentation on hacks that's available here makes upgrading simple, so long as you have a solid record of what you've done. If you don't have to be bleeding edge, just wait a week or few and someone will have tested and documented hacks. Worst case, you have to reapply hacks.
My experience has been that the small tweaks you do to customize your board are harder to recreate, and must be documented thoroughly. For example, I've saved txt files of each template customization I've made - states tmpl name, original code, new code, what the change actually did.
Don't forget, if Infopop support is important to you, there are support restrictions on a hacked board.
