According to IRS Publication 529:

You can deduct certain expenses you have in looking for a new job in your present occupation, even if you do not get a new job. You cannot deduct these expenses if:

1. You are looking for a job in a new occupation,

2. There was a substantial break between the ending of your last job and your looking for a new one, or

3. You are looking for a job for the first time.



So the question is whether starting your residency would be considered a new occupation. My gut tells me that is would be, which means tht your job search expenses wouldn't be deductible.

You're more familiar with all the facts and circumstances, however, so perhaps you can substantiate that starting your residency does not qualify as a new occupation for you.

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