Issue 1: Initialize on Precompile
The first issue stemmed from the following asset pipeline configuration parameter: "config.assets.initialize_on_precompile". By default, this configuration parameter is set to true. However, if you precompile assets for your test and production environments on your local machine before deployment, you may not be able to connect to those environments' databases and/or other dependencies. Other steps that occur during initialization for those environments may potentially fail as well.
One potential work-around is inserting conditional "unless ENV['RAILS_GROUPS'] == 'assets' " statements throughout your code. When you run the rake task, 'rake assets:precompile', behind the scenes the RAILS_GROUPS environment variable is set to 'assets'. Conditionally checking for the existence and value of this environment variable can allow you execute or not execute certain bits of code. However, this solution may not always work or you may not actually want these conditional statements throughout your code.
Another option (and my choice) is to create a special 'asset' environment file. In your application_root/config/environments directory, you probably already have development.rb, test.rb, and production.rb files (or some variation of those environment files). Why not create a bare-bones "deploy-assets.rb" environment file that only has the stuff you need to precompile your assets? You can leave "config.assets.initialize_on_precompile" set to true and not have to litter your code with the previously mentioned conditional statements. If you go this route, you'll simply call "rake RAILS_ENV='deploy-assets' assets:precompile" to precompile your assets.
Issue 2: Rails Relative URL Root
I mentioned above that my local development environment has a different context root than the test and production environments. If different a context root is something that you need to account for when the application is initialized, you need to set RAILS_RELATIVE_URL_ROOT when calling the assets:precompile task. The complete command would look something like this: "rake RAILS_ENV='deploy-assets' RAILS_RELATIVE_URL_ROOT='/applicationRoot' assets:precompile", where "applicationRoot" is the your application's context root. It's a simple and easy fix, but I didn't see it mentioned in any of the asset pipeline guides that I read through.
Issue 3: Verify your assets actually precompiled
If you precompile the assets and it appears to succeed, but you're seeing "resource not found" exceptions, asset precompilation may be failing silently.
I like the asset pipeline. My application's home page requests were cut in half due to the condensed application.js and application.css files which in turn improved speed. The few issues I mentioned above aren't hard to overcome, but they did take some time to track down. Hopefully if you're experiencing the same issues, you will find these tips helpful.