Kim, if you want to keep the pool liner (til the college is done), patch both the outside and the inside - it will provide a better and longer lasting seal. You could also 'double patch' the interior side (1 patch over the hole and another, slightly larger patch over the first one - be sure to 'round off' the patches so that it is less likely that something can rip them off.)
For ?#1 - there are a number of products that will kill anything that may try to grow up under the pool. Rock salt may keep anything from growing or 'rooting' under the tarp - it should kill any grass or weeds and 'discourage' larger plants/ trees from spreading their roots into that area.
If I've missed someting in your post, please ask for clarification - I, and all the others here, want you to have another 'trouble-free' season with your pool!!
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