I started a new thread with your question to attract more "eyes."
re: I want the easiest entry into all of this
When it comes to Painter make no mistake:
There is no easy entry. It is a very, very feature rich and, therefore, complex program to learn and use.
In addition to the software, training is a must. No way to learn to use it by intuition. Look into very high quality, but low cost online offerings at
www.EclecticAcademy.com.
Since Painter is
'Essentials on steroids,' what limitations has she found with Essentials?
FWIW: I've used IX, upgraded to IX.5, removed the IX.5 upgrade (it was XXXX). Have X now; fairly stable compared to IX, IX.5. If you determine she needs to move beyond Essentials, I'd recommend X.
Just checked eBay; some very, very good prices on Painter X.