In response to the OP, yes the hair can clog the filter. As was mentioned above, try to see if they will let you be proactive and brush the dog really well before, as well as clean up after your dog swims.
One of my friends used to swim his chessie in the neighbor's pool. Nothing is more upsetting than a bunch of brown, curly hair floating in the water. LOL... Even if you know where it came from, it is just gross...
I have yet to see a shop vac with a reverse in a long time. If you do that, it would need to be a model that you only used for that purpose. I think you would be better off to just get a dog dryer. They blast the water out of a dog's coat and are made for that purpose. It will cost you more initially, but they last a long time.
Brushing or blowing out with a shop vac before the dog gets in will definately help.
Keep nails short, and train the dog to use the stairs to get out of the pool to avoid any pool-liner related catastophes.
As others suggested, skim the pool after each swim to help collect any hair.
I don't have many friends with swimming pools, but these are the steps I take when we (dog and handler both!) are invited to a pool party. Tessie naturally loves to swim, whether it's the beach, a pool, or a pond.
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