R. I just wanted you to check it out to show you how very chalk like a casual sketch can be using the Painter software. The cars you commented on that you saw from me, were also completely done in Painter as well. But with airbrush and markers.
Spending a bunch a money on stuff your are unsure of is difficult. I would say, when you bought your Wacom bd, you get painter classic. Mess around with that and ifyou reeeeelly like it, then step up. If its just ok, maybe everything you need is in Photoshop that you already have.