I started working as an independent contractor in January for the first time. My main gig averages about 30 billable hours per week and is a clear 1099 situation. I think I have a good understanding of what I can deduct for expenses, insurance, etc on the 1099 front.

I've now taken a second gig doing side projects on an "as-needed" or "time-to-time" basis. The client preferred a W2 and I agreed. Now I'm wondering what the impact will be on deductible expenses, insurance, and healthcare if 15-20% of my overall income is W2?

Two main questions, really.

A) what exactly can I claim for unreimbursed expenses for the W2 gig? Commuting to the employer office is out, but what about driving to the next town over to meet a 3rd party customer for a project? What about that 2 hrs spent working out of a Starbucks, or grabbing lunch en route to the 3rd party customer's office? What about the 15 miles I drove to pick up the computer desk I bought?

B) do I have to prorate my insurance premiums, out of pocket medical, equipment (computer and office supplies, mostly), and cell phone bill between the ~80% 1099 and the ~20% W2? This is the big one, especially since I'm anticipating significant out of pocket medical for my son this year.

I hope this post is simply thorough and not over-complicated. If it's the latter, my next move would be to consult a tax pro.

As a W2 employee they should be paying your trave expense and business costs And lunch meals working a W2 are not deductable but should be paid if you are meeting clients by the company employing you.

You need to keep all costs and expenses separate, all milage separate and even best if you don't use business equipment for any personal use

You can deduct your 1099-misc business related expenses on schedule C or C-EZ.

Business related expenses for W2 income are deducted as itemized deduction on schedule A.
You will take deduction only if your itemized deductions are more than your standard deduction. You can deduct the expenses that are more than 2% of your adjusted gross income (Form 1040, line 38). Read: Your U.S. Tax Return: Itemized Deductions