Hi Mike, I grew my own psilocybin mushrooms many years ago in 2007 and I will do my best to answer your questions:
How the ripe mushrooms look depends on the strain — but in general, they look like the images on the article. You want to pick them just as the caps start to open — it should be fairly obvious (when to pick) when you have the actual mushrooms in front of you.
Dosage — always be cautious until you are sure of how dosages affect you personally and dosage is dependent on strain, size etc. Personally, I tried half a cap the first time, it was a light experience. It’s wise to use the edibility test the first time you are consuming mushrooms — this is more for picking wild mushrooms but it’s useful for psilocybin first timers.
Yes you can get multiple harvests from each cake if you keep the cake moist (after your first harvest) — there might be other conditions I’ve forgotten, Google is your friend!
Hope this helps.