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As a sole proprietor you may do that. I wouldn't recommend operating that way as it makes harder to prove what income and expenses were for the business as opposed to something else. If you pay your spouse for the work and she's really an independent contractor then she'll have to be issued a...

Hello, I live in IL. I I'm just a sole proprietor with no LLC, S Corp, or EIN. My question is can I as a sole proprietor issue a 1099 for someone that has done work for me? I personally use TurboTax Home and office and it gives me the option to give someone a 1099. I am probably going to...

Thank you for a very detailed response and examples. You make a lot of great points abd definitely bring up a lot of questions I need to ask myself. Such as is it worth it. I appreciate all your help as always. This not being my first post and this not being your first wonderful...

Hello, I live in IL. I have teenager 15, almost 16 years old and wants to start working. I am happy they want to start working. I receive SSDI for myself. My Child / Teenager receives half of what I get from SSDI. Will their income from any jobs rather its a W2 or 1099 affect either my...

Hello, Appreciate the advice in advance. I live in IL. Married filing jointly. I have self-employment income. I am just using my SS # and not an EIN. I of course receive either a 1099-K or 1099-NEC from companies I work with. All via direct deposit if that matters. My question is it...

Hello, Thank you so much for all the help information and links as well . You have helped me more than once in this site and it's greatly appreciated not just by me, but I am sure many others that probably have the same question. Thanks again!

Thank you!

Hello, I didn't see a "Tax" section, so sorry if this in the wrong section. I am married and file jointly. My wife has a W-2 job and does Door Dash a little bit through the year. I do freelance I.T work and file a 1099-K or 1099-Nec depending on which companies I do business with. My...

Hello, I had a few questions about Per Diem. My State is IL. County is Cook. I do I.T work and a lot of the work starts in the evening and goes well into the next morning / day. I only bring this up because I am not sure how that would effect my Per Diem if I can take it at all. I dont have...

Hello, Thank you for a quick and detailed response. That definitely helps! Have a great day.

Thanks for the help in advance. If it matters this is in Cook County in IL. I bought a new car in 2023. Traded in a car that I still owed about $300 on. (Trade in was $3700, I paid the $300 difference to the loan company that had the title ) I received a ST-556 from the Car Dealership...

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Thank you!

I am on SSDI as well as Self Employed. I am asking this question because Social Security says they want the gross amount earned. That is what I am trying to figure out. To my understanding as an Independent Contractor there is no Gross and Net like a W-2 Employee. This all is filed just under...

I appreciate your quick response. Is there a link that I can reference? Thanks again.

Hello, The person on SSI instead of SSDI is because of the lack of any work history and not being over the age of 62 years old or older. Thanks

Hello, I wanted to know if SSI benefits would be reduced someone on SSI (Age of 54 years old) was to marry someone that has only worked for the United States Postal Service and only receives a Pension from the work done with the Postal service)? (Age of Retired Postal work with the Federal...

Hello, Thank you for the quick and detailed response. It is much appreciated! Thanks for the additional link as well and the link to the tax section. I will talk with a CPA to make sure it gets done correctly. Thanks again!

Hello, I didn't see a tax section so I hope this section is fine to post in. Details: In the State of IL County: Cook Bought July of 2020 I am the first owner of the Van. Only had 4 miles on the odometer. Van is under 6000 pounds. Cost of Van with Tax, Warranty Ect was around $28,600 Placed...

Hello, Follow up question. Is there a way to request more time from the court to have more time to possibly get an attorney if I can find one I can afford, and/ or just more advice before my court date? Is there usually a fee to file such request for a different court date for more time to be...