For example instead of getting the DV888 I get the California.
A yoyo’s size usually would better harder to do tricks unless its insanely large or small.
(A California would not play worse cause its larger than the DV888 but if you prefer a certain size you’d probably be better with that size.)
Yeah… its all preferance… I truly prefer larger, heavier yoyos, so I often find my self messing up on tricks with a small yoyo, that I’d nail on a big clunker…
If you have absurdly small string segments, certain movements can become difficult, but you should be able to handle anything your yoyo throws at ya 
i love small floaty throws, you may not. It really is all about preference.
For really techy tricks, yes, it will be slightly harder. You can still learn them on a big yoyo, but it won’t be as easy.