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My last employer has asked me to come back as a 1099 contract worker to help them out due to being shorthanded. I live in Missouri and the company is in San Francisco. I'm trying to figure out if I rent a room from someone for several months, would it be tax deductible?
I would be flying in to San Francisco and staying about 15 days, then returning back to MO for about 20 days. I think the rent would be tax deductible, but just want to make sure.

I'm confused. You want to rent a room for several months, but you are only going to be in San Francisco for a couple of weeks? Or is this going to be 2 weeks in SFO, 3 weeks back in MO, 2 more weeks in SFO, 3 more weeks in MO, etc.?

If it's the latter, then you can deduct the cost of the room for the time that you are staying in SFO, but the cost for the room while you are staying in MO would not be deductible, since you would be back at your tax home during that time. So if you are renting on a monthly basis, based on the 2 week/3 week cycle, you could deduct ~40% of the total cost - probably a little more, since you presumably would have 1 more 2 week stint than you had of the 3 week stints.

Note: Since presumably you will be paying more than $600 in total rent, you will have to issue a 1099 to the person you are renting a room from, so you need to get their SSN, address, etc.

I would strongly suggest that you just pursue having the company pay for your lodging while you are in SFO - either in a hotel or a furnished apartment. (Many companies have standing arrangements for furnished apartments for new hires, contractors and temporary employee moves.) Even as a contractor, the company I worked for always reimbursed me for travel expenses, if they didn't pay for them beforehand. If they want you badly enough, they will pay.

I hope the hourly rate you negotiated as a contractor is significantly higher than your rate as an employee was - like twice the rate if they are paying for your travel, and if you're having to cover your travel, enough more per hour to pay for that. If they're not paying that much, you're giving them a much better deal than they had when you were an employee, and they're probably not pursuing a replacement as aggressively as they should be, at least if you actually want to stop working for them. If you continue to give them such a good deal, they will likely continue to be 'shorthanded' until you refuse to go back.

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