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I don't know too much about taxes in general, so obviously I plan to discuss this all with my tax preparer, but I don't know yet how much he knows about gambling.
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This is a key issue. I've met a bunch of tax people who know very little about the proper way to handle gambling and taxes.
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What books are worth reading in order to learn more about the subject?
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First, definitely check out Russ Fox's blog on the subject:
http://www.taxabletalk.com/gambling/
Fox knows this stuff as well as anyone I've met.
Walter Lewis wrote a book called "The Gambler's Guide to Taxes". I haven't read it yet, so I don't know if it's any good. It probably raises some good issues.
The same is true for Chien and Scott's "Tax Help for the Frugal Gambler". I haven't read it so I can't tell you if the information it contains is good, but at the very least it probably addresses important topics. I expect that both of these books are worth reading.
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I plan to file recreationally this year, but probably as a pro next year, if that matters. Thanks.
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I'm not a tax professional, but my understanding is that there are both positives and negatives to filing as a pro. On the plus side, a pro gets to net wins and losses and can deduct reasonable expenses. On the down side, you have to pay self employment taxes. Without seeing numbers, there's no way anyone can say for certain whether filing as a pro would make sense in your case or not. These are probably the sorts of things you seek to learn.