It depends on what you consider work. I relaxed my hair for 20+ years and just went natural last year. I find it WAY easier with my hair natural. My hair sits right above where an average bra strap crosses the back, so its a decent length. I find it easier because I don't have to go to the salon as often, can go straight or curly. So if I'm feeling lazy I can wash, condition and go and still look nice.
I've never gone very short, but know lots of people who do and have. From what I can gather from them part of it depends on hair texture, so if your hair has nice natural curls they can just wash and go; all they need is a little gel or mousse. I know others where the cut it self requires that a stylist curl it and that is work. Did you ever watch divorce court when it first came out with judge Ephriam? Her style requires a lot of work.
Wigs are fun and allow you to change your hair temporarily, sometimes I want a short style for a few days, so I wear one. That's more for fun than ease.
When I want my hair straight I press it, it keeps for about a week or so unless it gets wet.
Braids are carefree, once they are in, but it takes a long time to get them in and the smaller the braid the longer it takes. Also individuals vs. a cornrow style takes longer. Plus it takes FOREVER to take them out!
Weaves, depending on the type, can be easier. Thing with them is that to get a nice one, that doesn't scream " I'm wearing a weave" can be pricey. You still have to take care of them although I see far too many people who don't :P
The biggest benefit of relaxing your hair is that it is straight so if your hair has tighter curls, that are hard to manage, it makes it easy to manage. If you have really thick hair, it can make it seem thinner and therefore easier to handle. My hair isn't super thick but once relaxed it's thin.
Relaxers are NOT carefree either. You have to get touch-ups on a regular basis b/c the curly growing against the straight causes a weak point and if left too long will break off. It is a chemical and often dries hair out and makes it weaker so deep conditioning etc is very important. It's also very expensive, at least in my area. To maintain mine, when I had it, was almost 300 a month: 120 for the touch-up( every 6-8 weeks), 60 dollars for a wash, curl every 2 weeks, plus tipping the stylist. So some months it was only about 180 but still.
Also not everyone looks good with short hair, no matter the nationality.