New Startup Advice In "Taxachusetts"


Registered Member
Dear Fellow Freelancers,

As many probably are more familiar with the laws, I would truly appreciate any advice on a new startup plan. Here is the scenario: I am a college student, who having planned to freelance during high-school, got caught up in tax regulations/questions (college prep took all of my time). Since it is summer, I am considering to attempt freelancing, as I am on LOA until Fall. I have a job, but am not working yet. Summer jobs are harder to find in my hometown if you only want to work seasonal, and if it were to work out then I would leave my current position to do Fiverr, Upwork, art shows, and some custom sites such as Game-Crafter and Etsy.

Here is what I have so far as plans:
  • Our city has the exemption to allow artists to work at home for residential zones
  • I know where to go purchase a business license
  • Intuit Quick-Books would most likely work for my accounting work
  • I am covered under my parents insurance for now, as I am living at home
  • Side hustling an Ebay store would help with income
  • I would use open-source such as Libre-Office, and Inkscape, etc. for legal ramifications (i.e. no royalties, licenses)
Questions I have:
  • Massachusetts Independent Contractor law, do other smaller sources of income, such as AmazonTurk (not a good example), count as working for an employee?
  • If out-of-state clients purchase your services, are their dual taxes? Or is that only for out-of-state employment? I assume sales-tax is a factor?
  • Since I am classified as a dependent, how would this affect property taxes working at home? I would not claim it on my taxes.
  • Is their an increased property tax when you work at home?
  • Besides income tax, self-employment tax, sales-tax, are there any other taxes I am missing?
  • Is it safe to freelance projects without officially copy-writing every work? Dangers?
  • Insurance requirements?
  • Legal needs? Do you have to have a lawyer? Why or why not?
I know this is a lot, and I am sure I am missing something. Any advice at all would be amazing! I will look forward to any replies. All I really want to do is work on smaller projects for people, such as design logos, but I don't want to miss anything, or else I could lose more than I'd make! Thanks again.

- graphx4life