I just got off the phone with a prospective employer in my field who has a telecommuting position that sounds like a good fit for me. I would need to file as a 1099 which I have never done before. I’m reading what I can find about 1099’s online and plan to hire some professional tax help (for this and the music company we are trying to get off the ground for Mrs. WeHaveCookies), but of course I’m dying to know what my fellow Dopers have to say about their experiences.
Some questions off the top of my head:
Mrs. WeHaveCookies just bought (from our joint checking) a printer/scanner/fax/copier for her home-office job (which is not a 1099) and I would be wanting to use it as well. Would I be able to write it off even though it was purchased prior to my entering 1099 status, assuming I get the job?
Is there any sort of limit to the amount I can write-off for home office purchases in proportion to my salary? I’m not going to go nuts, but I will need a new puter and I have my eye on a mac…
Can I still work other non-1099 jobs part time, or multiple 1099 positions for multiple employers?
How much of a headache is the quarterly self-tax stuff?
How much of a headache is the self-insured stuff?
I’m stoked about this opportunity but not so stoked about having to take a crash course in an employment/tax/insurance arrangement that I’m completely ignorant of.
Any assistance/opinions are appreciated.