RE: Getting my bot to ask a series of questions

Using a script would be the easiest way to do this.

You can either use Self, or AIML.

There is an example here in our script library,

https://www.botlibre.com/script?id=11694448

It is used by the Turing bot,
https://www.botlibre.com/browse?id=11694422

For Self syntax see,
https://www.botlibre.com/forum-post?id=705860

Basically you want to record a variable on the conversation to track the current state.
You could also use topics.

For AIML see,
https://www.botlibre.com/forum-post?id=705870

In AIML I think you may be able to use topics for this.