Jspence,
This is all a set of questions that only you can actually answer.
You can plan what ever you can dream, and if you can drive the dream - So Much the Better.
You don't say what you are driving and if you are OK with all kinds of overnights. Planning where to overnight can be a big issue. If you have a large coach or trailer, it just won't fit everywhere. How well self-contained you are makes a big difference also.
Yes, as one above noted, a long excursion is just a bbunch of short excursions in close coordination.
Matt