Your situation is not similar to the original subject of this post. To increase your changes of getting the help you need, I suggest you start a new thread. You should include dates on when you started renting rooms in the single family home and when you started using the condo as an office. There are also criteria that must be met in order to deduct the office expenses. You will need to figure the percentage of space you are using as an office in the condo. I doubt you can claim the entire condo as an office.
Your situation is complicated and I am not a tax expert. With that in mind, this is what I think. The $34,615 deductible mortgage interest you figured using Pub 936 would be the amount of mortgage interest you can deduct on schedule A if you didn't rent part of one house and claim office usage in the other. It will be reduced by the percentage of each home not used as your main or second residence. Of the interest not deductible on schedule A, you will be able to deduct the percentage of the total mortgage interest paid on each home equal to the percentage allocated to rent and business use respectively.
