Okay, when you stop working, and you file a claim, you are told about certification for weeks of benefits. All weeks, for unemployment purposes, in all states, run from Sunday through Saturday (with some very rare exceptions). All certifications you make refer to work done during the week you are certifying for, specifically. They are not interested in your income, as such, during that week, just pay that you have been paid, or will be paid at some time (regardless of when) that you made by working THAT WEEK you are doing the certification for.
Thus, if the company rattles around and a week after you stop working, gets you your last paycheck, or money from your vacation weeks, during the first or second week you are not working, you are not to report that money because you did not work out that money that week. If you won the scratch off that week, or mowed your neighbor's lawn for pay, or were paid for some weeks of owed wages that you'd actually worked out three or four months earlier, that is not to be considered work you have done during that week you are certifying for that must be reported as wages earned that week.
If you do your second week's certification, and you've received this vacation pay check and you (incorrectly I believe) report it as wages worked out that week, it will simply stop your claim cold. They don't know anything except that perhaps you've gone to work at another job and had worked all that week and are done with unemployment benefits now forever. Before you could make a next week's certification, you'd have to go in and re-open your claim. This would simply start the process again and you would have missed a week's being certified, and possibly getting restarted again for a while. And they are NOT interested in work you're being paid for or vacation time you're being paid for that was done a long time ago.
But I am in favor of your, just for the sake of correctness, you call someone in the actual system, not on line, or if there's an on line question section, or customer service section, you need to clear this specific question with a department of labor in your state person. Preferably a living human being in the system. Hold the line if you have to. But they're the ones to ask specifically. The same goes for working as a 1099 for someone. Discuss it with them, before reporting it or not reporting it. In each case, take a note of when you talked with someone, who you talked with, and what they told you.
Unemployment insurance is not a subsidy for anyone based on their needs or how much money you had to live on this week. It's based on whether you are separated from an employer through no fault of your own, and that you are able, available and actively seeking other equivalent work during that specific week you are certifying for. If you removed yourself from the labor force by working at your own business full time, you'd be disqualifying yourself not based on income earned, but from availability for equivalent. If you open your own business, you're removing yourself from seeking and being willing to accept another job. In any thing of this sort that you do or have questions about, again, run it by the unemployment insurance section for your state for a specific answer in your case. Youre jumping into this without real good understanding of the process from just reading the material. You also don't have enough specific information about this contract work you might do later right now.
At the beginning of your claim, you will be given or mailed or screened a personal Monetary Determination. This will show what, specifically, you will be allowed to draw based on your counted quarters of work. It will be something like, $435 for 26 weeks or a total amount of $11,310. If you did not have this eligibility, there'd be no reason to go further. But then, after your claim has set up monetarily, you begin making the weekly certifications, and then you should be started on the process of the system determining if you qualify for benefits based on your reason for separation. That's another ball of wax entirely.
You will have a waiting week first, that is one week that you serve and certify for that you will not be paid for. Then, if yours is a simple lack of work lay off claim, you'd be paid the first time after the second week's certification goes in. However, if you do not have a simple claim, if you were terminated for cause or quit your job, the employer will be contacted, the determination must be made, using what you say and what they say, whether or not youIf 'll be approved to receive benefits for the weeks of certification you have made. Generally, in a clean claim, you may receive your first pay in three to four weeks. In a contested claim, with appeals involved, four to six weeks is pretty quick. Keep making the weekly certifications.
Speak to someone in the agency about exactly what to do with reporting the vacation money. If you've already reported it, speak to them about the situation and how to reopen your claim.