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You could buy or make a wood plane. They are very cheap and easy to make square. They do take a little practice and time to set up, but I found that they are easier to use on the shooting board than my metal planes.
About wind. It is a good idea to check some point along the. But usually wind is worst at the end. A quick test is to put the board on a flat surface and simply see if it wobbles.
Diamond stones are much like sandpaper (but with a lot longer lifespan). At the beginning, the stones are very sharp. But that stops quickly and you will have a long periode of medium sharpens. It sounds like you entered the periode of medium sharpness on your stones.
To speed up your sharping, it is a good idea to sharpen very often. If you sharpen often (like maybe once every 1-2 working hours depending on what you are doing) you should be able to sharpen in less than a minute.
On an end note, you might consider moving to water stones. While a big initial investment and require flatting, and are more messy, water stones stay sharp all trough the it’s life and sharpens faster.
I have tried it. I used 25% ammonia in a small cup and put the wood in next to it. Depending on the size of the piece, it will take anywhere from 1 to a 3 weeks for the color to change all the way through. The final color will be darker the higher the level of tannin acid is. So if you want it really dark, you should probably use use the ammonia treatment before the wood is dry, as green wood have higher levels of tannin acid.
25% ammonia smells very unpleasant and can be dangerous. So please be careful.
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