I won't say it's easier, per se.
I will say you're less likely to get negative social sanctions for your decision.
Being tall and slender or petite and very thin with great fashion sense can be a part of this as well.
If I woman has great skin, even features, a slender body (SLENDER IS RELATIVE I'M NOT ASSUMING SLENDER EQUALS TRIPLE ZERO), a height attractive for your body type (TALL IS RELATIVE), great fashion sense, and confidence having a TWA can be a plus.
If you have okay or "bad" skin, are slightly over weight, don't always dress as nicely as you could, are extremely tall or short and do not "own" it, and your confidence rises and falls during the day then, no, having a TWA is not going to be a "cake walk".
I speak from experience on both sides of the scale. The first time I went natural I had scab hair, cystic acne, low self-esteem, I am petite and had a very quirky sense of fashion at the time (think Final Fantasy meets Victorian England). I was a size zero, however, which throws things in our thin-obsessed society.
This is the third time I've gone natural. I have flawless skin (Thanks to God and Accutane), I'm a curvy size two (lifting weights DOES make a difference ladies!), I've embraced the fact I adore girly things and wear heels, skirts and blouses daily, I own my 5'4-ness going for what I call the "Dolly" look, and for the first time I have confidence.
Having a TWA (outside of my annoying corn town) has actually become a plus. People actually walk up to me and compliment my total appearance. That has never happened before.
It's not right.
It's not fair.
I had the same value as a human the first time I BCed.
However, this time around (in bigger cities) its a boon.
Now I'm suddenly "modelesque". Never mind I'm 5'4!
Being "exotic" is thrown my way as a compliment, not a slight as it usually was (in my little corn town).
We HAVE been socialized to view long hair as a +1 for women. As other posters have said, essentially, the "rest of you" must be "on point" to be deemed "acceptable" with a TWA according to standards that never had us in mind during their creation and never will.
That said...long hair can only do so much for an unkempt woman.
It's not the be all and end all of beauty.
Not by a long shot.