I shed a tear while reading this, that was pretty wholesome thread. I wish I could suggest a server to you but I’m new and I play on “new player” server, I like it, it works for me. I’ll try to answer some of your questions.
I was looking at the “new player friendly guilds” and I think this guild might be for you:
Definitely play druid, it’s fun class.
If you join the guild I suggested I’m 100% certain the members there will be more than happy to give you tips and even level with you because they seem like a really wholesome people.
Any profession other than Engineering will be fine.
I honestly can’t wait to hear on your update, and I wish you nothing but the best.