I think seeing conditions should be taken into account and also the observers experience.
I've seen shadow transits a few times in my 8" too, and while Io is fairly easy to see, Europa can be a bit harder. Occasionally I've also been able to follow Io itself as it crosses the disc, but Europa is a bit small again for that in an 8".
If the seeing conditions aren't good you're going to struggle. I usually tell people that they have to be patient viewing the planets - depending on the night, you might get a period of 'wobbliness' then one to two seconds of steadiness where the shadow should pop out, then back to wobbliness for a while. Because of this it's best if you're sitting down and viewing to that you can put your full concentrating on looking at Jupiter and not have to worry about holding your body upright.
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