First off, I am sorry you are still stuck on 1.8.6, but making the transition is a must. I am currently doing a similar 1.8.7 to 1.9.x transition myself so let me share some info that I have been gathering:
The main thing here is that lots of stuff has changed. I am not sure how large your code base is but here are the facts.
- There are a lot of changes made to syntax and general structure. I have found this post incredibly helpful.
- Your gems will probably explode. Meaning that you will have to figure out your dependencies and see what is/isn't supported anymore.
- You need to make the transition.
To be honest #3 is the key. As of July 2013 Rails 1.8.x is not seeing support so security patches are not coming and you are missing out on optimizations that are years old. If you have any questions go ahead and ask.
I will most likely update this if I find any more useful information