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Re board sizes, there was a logical reason for a lot of different sizes in skateboards, the main one is no one is the same shoe size, leg length, overall height, etc.
Having them scaled from 7 x 30, 7.5 x 31, 8 x 31.5, 8.25 x 32, 8.5 x 32.5, 9 x 33 is all good and well, but what if there is someone who prefers a skateboard that is both short and wide, or someone else who prefers a skateboard that is both narrow and long.
Some woodshops and brands will do a board that is uniform all the way through all the widths, eg HLC I think does a 32 long with 14.25 wb on everything from 8 through to 9, whereas others mix it up a lot more and make many different shapes and sizes to go with whatever others want, eg DLX through BBS.
As to the reason for some boards being longer, the DLX board range used an alternating option in width through the range, so it would alternate between longer and shorter as you go, as well as having a few different lengths for each width in the most popular ones.
The most common sizes before things went Full or Full se were as follows:
8.06 x 31.8 with 14.38
8.12 x 32 with 14.25
8.25 x 32 with 14.38
8.38 x 32.25 with 14.5
8.5 x 32.25 with 14.38
8.62 x 32.75 with 14.75 wb
8.75 x 32.4 with 14.62 wb
Then the "Blue eagle" seemed to be the most popular size in the 8.5 x 31.85 with 14.25 wb board for a while, so everyone thinks that is the only 8.5, but there were actually about three 8.5 boards in rotation, some more common than others.
This is not even coming close to the whole list, yes there are the 8.12 short, 8.28 short, etc.
8.06 x 31.8 with 14.38 wb standard
8.12 x 32 with 14.25 wb standard
8.25 x 32 with 14.38 wb standard
8.25 x 32.25 with 14.5 wb for Full shape
8.25 x 32 with 14.25 wb for Full SE shape
8.38 x 32.25 with 14.5 wb standard
8.38 x 32.5 with 14.6 wb for Full shape
8.38 x 32.18 with 14.38 wb for Full SE shape
8.4 x 32 with 14.25 wb standard
8.5 x 31.85 with 14.25 wb short
8.5 x 32.25 with 14.38 wb standard
8.5 x 32.5 with 14.75 wb long
8.5 x 32.6 with 14.6 wb for Full shape
8.62 x 32.75 with 14.75 wb
8.75 x 32.4 with 14.62 wb
8.75 x 32.75 with 14.7 wb for Full shape
9 x 33.25 with 15 wb
Some of those dimensions might be a bit off (sorry) but the point I was trying to make is they alternate somewhat to give people options for width and length / wb.
In general terms, there is no right or wrong answer to what is the best size for your body size, shape, shoe size, etc. There are small guys I know with size 9 shoes riding 9" boards and still doing tre flips and everything else, as well as others in the taller category, size 12 shoes riding 8" and doing much the same stuff they did back in 2000s, cause that is what he skated then.
If you feel like a wider board is more comfortable, good for you, or if a smaller board works better for what you want to do, compared to a bigger board, longer, shorter, etc.
We used to always have this sort of conversation with people who came into the shop, sometimes with some customers who would get quite heated at each other saying there was a "true size" and then someone else was wrong or whatever, but in general terms an adult can pick what works best for them and I would never try to put someone in a pigeon hole just saying they were a ledge tech skater on an 8" or a bowl lord on a 9" or similar, which used to be way more the case back twenty years ago.
Before that, everyone rode more narrow boards as that was just what we did, no matter what terrain you skated, because there wasn't half the choice that there is in the current market. Board width overall has definitely gone from under 8" as standard to about 8.25 and bigger nowdays for most people I know, certainly my own boards 8 to 8.12 for a long time, now 8.38 and up.
*** Sorry if this turned into a rant, or has too much information. I didn't mean it to be like that, but more just to help with any confusion.