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Ok, I'll make this a long post to give all the info.

I left a company at the end of May. June 1 I went to work for myself. I worked out of a home office that is 100% dedicated to the business. I went on COBRA. I entered into a consulting agreement with a single company (not the company I used to work for), all billing/invoicing was done through that company. November 1st I became an employee of the company that I was consulting with. Therefore I received a 1099 for the work I did from 6/1 through 10/31 and a W-2 for the period 11/1 to 12/31. I am still on COBRA, the company has no benefit plan and I am still working out of my house.

I am using TaxCut to prepare my taxes.

1. When asked about home office expenses, I assume I have to complete two seperate forms, one for each period. I also assume that the amounts for things like utilities (direct and indirect) are for the period time for the form only, for example an indirect expense for the first form would be the electric bill from 6/1 through 10/31. The program also asks me about insurance costs associated with the property, can I deduct my PMI as well as my homeowners?

2. Where is the appropriate place to deduct my COBRA premium payments. Is it more beneficial to deduct it one way, rather than another?

3. Is there anything else that I should be looking for to help with increasing deductions.

Any help or advice is appreciated!

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