I had some time to think about this the other day and was writing down some notes and thoughts regarding the issue.
I want to say that by no means do I consider any style to be “better” than another. For all styles have a very unique substance that makes them all very impressive and highly respectable. That said, I do think perhaps some styles might be possibly “more difficult” than others, and I thought I would see what the rest of you thought of my ideas.
Breaking down the styles, I start with the most familiar style everyone is familiar with.
1A.
No doubt the most widely played style, and of course the “standard” style for many since even exclusive players of the other styles start out with this style. Easily, single A is the most competitive division where we see well over 100 competitors at numerous contest all around the world. And with players seeming to push the limits of play on a daily basis through showcase videos on youtube and the trick circle on instagram, its easy to see that to make a name for yourself in this style, you have to REALLY stand out and push things to new limits. Although difficult to be noticed by the saturation of 1A specific players in the yoyo world, 1A also is the style with the most resources to learn and obtain new concepts and material. Here on the site, as well as all over youtube, there are countless numbers of 1A tutorials where players can pick up new ideas and learn.
5A.
Freehand to me seems to be a style that many pick up and mess around with once they have come proficient enough in 1A. It adds another element of a moving object that needs to be manipulated along with the yoyo itself, meaning that the player must keep track of two objects at once and understand how both objects can correlate together to create a complete trick or combo. 5A has a large number of players although the crowd is not as large as 1A. Although not as big, it seems that most players will dabble in this style for a bit just for fun at the least, and once an understanding of how a counterweight reacts with a yoyo, players seem to be able to pick up the basics relatively quickly, although moving into harder original tricks can take a while. Although not as many resources as 1A, there are quite a few good 5A tutorials here and there. For the most part, after the “basics” it seems that players are expected to simply make up and create, which is also the case for 1A, but perhaps not as much.
4A.
Offstring yoyoing is a division that I have noticed is not as big as 1A and perhaps 5A, but seems to have a very clear dividing line between who is “good” and just “average” that I see more so than 5A and 1A. The learning curve in 4A seems to be a bit rough at first as now the player is dealing with an object that if missed on a string, will be sent rolling away, forcing the player to restart, and completely start the trick over from the beginning. Mistakes are unforgiving. Where as in 1A and 5A, a missed string or a missed catch can be “repaired” by remounting, or undoing, a mistake in offstring results in a complete do over from scratch. Basically, it’s very hard to “cover up” a mistake. There are some resources here and there similar to 5A, although not anywhere near as much as 1A. Lots of hitting the tricks seems to be more muscle memory and precision than “knowing what to do”.
3A.
3A seems to be a smaller division with not too many competitors compared to the other styles, which makes sense to me as the way I see it, it is twice as difficult as 1A as we now add another yoyo. It goes beyond just adding another element as 5A, for now not only do we need to follow two objects, but we also must keep track of keeping planes, balance, and hitting strings, all while doing the same thing on another yoyo on a different hand. Two yoyos, twice the difficulty. Unlike the other styles, there are almost NO resources to truly pick up this style. Players who find themselves delving into the style are often forced to learn many things on their own, and try things that they see professional players do on stage or in videos. While not having the same sort of “unforgiving” aspect of missing a string in offstring, a missed string in this style can result in some very ugly and cringe worthy knots and tangles. When you add that second yoyo, it adds just another item to cause a really bad incident.
It seems to be a style that some may dabble in, but not many will actually take to it seriously.
2A.
2A is a style that seems to have a VERY distinct line between who is good and who is novice.
Similar to 3A, it also adds another element of a moving yoyo in addition to the first, but on top of this, 2A takes a completely different sort of yoyoing and forces the player to do such style on both hands. I have met numerous very skilled players of other styles who could barely do single hand loops, as it is a totally different sort of animal. The learning curve of 2A seems very long, with some players going years just to get down clean two handed loops, which is only then just the most basic stepping stone into the world of that style. Many players may attempt it a bit, but it seems that very few actually take the time to take it on and progress past the basics. Like 3A, there are almost NO resources for this style, and unlike many of the other styles, it is based completely on muscle memory, as what needs to be done is usually quite clear, but actually pulling it off is another story entirely.
For myself, the way that I see it is that these styles can be listed as such in terms of least to most difficult:
Least
1A
5A
4A
3A
2A
Most
These are based clearly on what I see around the yoyo world. I am almost strictly a 1A player, do a bit of 5A for fun sometimes, rarely throw offstring, only tried 3A once in my life I believe, and own two unleashed but can’t seem to get loops down yet. So by no means are these assumptions only based on what I experience myself. 
Would love to hear some other options on this!
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