These guys have prepared my returns for the past 6 years. http://www.edaytradertax.com/ Many of your questions are answered on their web site. Bob and Simona should be able to answer any other questions.
I would suggest Rob Robinson at DiMaggio and Robinson 312 - 658 - 1000 (ext. 20) Rob can easily guide you through your issue at a reasonable price. I have worked with him on far more complicated issues and I have been very happy with the results.