First, I'm a jerk. I have strong opinions about D&D and the TTRPG hobby. Most of the time my opinions are unpopular even amongst the most enthusiastic fans. Sometimes it's questioned if I even enjoy gaming at all.
To jump to the current situation and topic at hand. I've been asked to introduce a new player to D&D. She is enthusiastic about the hobby, watches Critical Role, etc., but has never played. It's important to me to try to put my biases aside and give this person a fair chance to fall in love with this hobby. I don't want my grognard, anti-WotC, anti-5E mentality to push away someone who could become a lifelong fan.
You on here wouldn't want that either, I'm sure. So I want to listen to your feedback and tips to help me get out of my own head and be welcoming to this enthusiastic new player. (She is a coworker of some of my other players.)
Some specific questions...
5E or 5.5E?
Or Shadowdark?
Start at 1st level or 3rd?
Should I try to streamline the character sheet?
Pregens?
Should I try the Starter Set? (I'm concerned because it's not really like how the actual game is played - with cards and components that don't really support the rest of the experience outside the starter adventure.)
Any other tips you'd recommend?