Hi Steven,
All the 4 points can easily be covered by Mappoint.
Just begin your project and a lot of people here will be pleased
to share their experience for some precise questions.
If you want to save time, begin with this book. It is not expensive and
you will have a lot of examples to be started.
http://www.mp2kmag.com/mp4dummies.asp
My main job is not programmer and I've learned to use Mappoint in
4 weeks with a very useful project for my business. And I am still learning here.
Good luck