In Minnesota I did not collect unemployment on the weeks I freelanced. In MN you still qualify for unemployment if you work less than 32 hrs a week and/or your income is less than your unemployment payment. My freelance was almost always below 32 hrs a week and always way more than the unemployment payment. If you make less than your unemployment payment, I think you get a certain percentage of your unemployment paid, but I have no experience with that. I’d go for a month without collecting unemployment without a problem. After the weeks where I worked more than 32 hours, I had to go through an extra step of “re-applying” for unemployment on-line which was not a big deal: I had to click a few radio buttons explaining the situation.
Basically, report the week you work on, not the the week you get paid on. When reporting, I did not list myself self-employed, I registered as working on-call or part time with specific companies I was working for.
I’m not sure how similar WI is to MN when it comes to this issue, though.
eta: While I was not collecting unemployment for a few weeks, I still was reporting weekly that I were working, but it is a part-time arrangement.