I am using TradeMax for the first time, and have manually entered the baseline position. Since this is an original baseline entry, should I write in the year that the Buy to Open trade was done or do I have to put in 2009 to obtain a 2009 tax report?

When holding baseline positions and using TradeMax for the first time, each open position must be manually entered into TradeMax prior to importing  the trade sequences for the current tax year. Manually entering the open positions after importing your current year trade data will cause trades to be mismatched. (i.e.: TradeMax cannot possibly match a sale in 2008 to a purchase in 2007 or earlier if the purchase has not been entered first.)

When appending Baseline position in the Append dialog, select the checkbox called TRADE INCLUDE IN YEAR and select 2009 when entering the FY2009 baseline. The baseline position will be viewable in the Baseline View under Financial Year 2009. If not done properly when inputting the Baseline position, the trade data cannot be viewed in Baseline view and the trade data will be mismatched. Alternately use the Trade Edit function to change a normal trade to baseline position.