<p>I have a Rails project which I neglected to build tests for (for shame!) and the code base has gotten pretty large. A friend of mine said that RSpec was a pain to use unless you use it from the beginning. Is this true? What would make him say that?</p>

<p>So, considering the available tests suites and the fact that the code base is already there, what would be my best course of action for getting this thing testable? Is it really that much different than doing it from the beginning?</p>

Maybe start with the models? They should be testable in isolation, which ought to make them the lowest-hanging fruit.
Then pick a model and start writing tests that say what it does. As you go along, think about other ways to test the code - are there edge cases that maybe you're not sure about? Write the tests and see how the model behaves. As you develop the tests, you may see areas in the code that aren't as clean and de-duplicated (DRY) as they might be. Now you have tests, you can refactor the code, since you know that you're not affecting behaviour. Try not to start improving design until you have tests in place - that way lies madness.
Once you have the models pinned down, move up.
That's one way. Alternatives might be starting with views or controllers, but you may find it easier to start with end-to-end transaction tests andwork your way into smaller and smaller pieces as you go along.