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1. Is it a painful process.
No
2. Does thumbincluder still work with 4.8.1?
Since this is a hack no direct answer. I assume not though since the fields to pull the thumb info in the photos table has not changed. However there are about 10 different versions of that hack flying around.
3. I have 4 skins on the forums. Will whatever skin the member uses on the forums now display when they visit the gallery?
Yes just make sure if your CSS is using gradients and such you correct any relative url's to full urls within the css file itself
We only integrate with CSS set as files also since displaying CSS inline will not work since we do not autoload the Invisionboard header.
4. Are there any important issues I should know about before proceeding
Nope just follow the upgrade instructions
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