Here Are my answers to your checklist

1) Preorder Heavensward
2) already saving Gil for new gear
3) trying to level doh/Dol and monk
4) seems like a good idea
5) since I don't have a main job ( can't decide) I'll probably go machinist/Astro
6) will be joining a free company
7) booked 4 weeks holidays
8) I already have too many ventures
9) will be cappedon gc seals by then
10) if I remember to watch your stream, i wll