Looking for some help with this tiered crossdressing dare
 

Hello all, I request your assistance with this dare. Something along an easy, medium, and hard difficulty for each section fits my theme. Extreme optional. A points system for each section could be added. Also for online shopping, any specific items would be nice to get. (maid outfit, school girl outfit, etc.) Also specific brands, good cheap options, more variety (different bras, panties, tops, bottoms), and more detail would be nice.

Clothes Required (cumulative):
Easy: Panties, +1 other item
Medium: Add leggings or stockings
Hard: Add skirt and sports bra
Extreme: Add makeup and wig

Shopping and 1st task:
Easy: Order online and take a picture of yourself.
Medium: Order online and go on some video chat websites.
Hard: Buy clothes IRL, don't lie if someone asks about them.
Extreme: Buy clothes IRL, try them on, ask others how you look, etc.

Humiliation:
Easy: ?
Medium: ?
Hard: ?

Anal:
Easy: ?
Medium: ?
Hard: ?

Punishments:
Fail 1 part: ?
Fail 2 parts: ?
Fail 3+ parts: ?

Tasks:
Easy: Wear small butt plug and panties in public
Medium: ?
Hard: ?

My limits for this dare include posting face on social media, any sort of hook-ups, and permanent changes (not shaving). No chastity devices please.