Complex situation, not sure how to file?

Hi there, 

 

Thank you all for taking the time to answer these questions! 

 

I have a bit of a complex situation. During 2021, I had quit a few major life changes.

  • 1) I was on unemployment
  • 2)I got off unemployment because I finally got a new full time job. However, this new job is in a different state from mine, so I have been working remotely. (I am in Maryland and my job is in Oregon) So I am not sure how to proceed with my taxes in that regard. I filled out Maryland tax forms for this job.
  • I started a small business that has slowly progressed.
  • This is the biggest change: I won a competition that paid my $100,000 dollars of my student loans. The money was not directly given to me. They were directly paid to my loan provider.  They also gave me a check for 20% of what they paid to contribute to the taxes.  1) How do I determine the taxes I owe for this competition if the money was not directly given to me? Do I report this as income? How do I report it? 2) Since they directly gave me a check for the money, am I supposed to report that and does that become taxed too? I have not received a 1099 from them. 

I am just wondering how do I go about all of these new changes when filing? 

 

Thank you

Alexis