@EnjoyIt – I apologize for overlooking your list.
1) You would need to hire your spouse for group health insurance (some insurers do this) in a sole proprietorship. In an S-corp or LLC, you, as >2% owner would include the cost of health insurance in your W2, which would then be deducted on page 1 of your form 1040, so it’s a wash. In a PSC, you would be treated as any other employee (non-reportable health insurance benefits).
2) Not true. In fact, there are limitations on self-rentals in an S-corp. A sole proprietorship is the best form for deducting home office expenses. That said, I have yet to see that you are better off using the $5/foot shortcut unless it is a very small office in a relatively inexpensive house.
3) If you have a home office and pay to park elsewhere (not as an employee but for work as a contractor), you can deduct parking, tolls, public transit, etc. as a sole proprietor. As an employee of your corporation, you can do the same, but I recommend an accountable plan.
4) Yes, you can establish a DB plan as a sole proprietor.
The medicare tax may be the main tax benefit but the reason for setting up a corp or LLC is not mainly for tax savings but other intangible benefits, such as protection. Having a separate entity makes it far easier to transfer part of your business to partners, too. Hope this helps.
This helps a whole lot.
My tax guy has me set up in two corporations
The PLLC taxed as an S-corp which takes in all income and pays a salary to me as well as 401K contributions. There are business deductions there as well.
He then had me set up a C-corp where it manages the business finances such as medical, home office, and car reimbursement.
I am starting to think that this tax person created a lot of complexity with the C-corp with absolutely no benefit.
Although this year and next year I opted to pay my fiancé a small salary to help manage my business out of the C-corp. She is a student and gets some very nice deductions. By going through the C-corp I did not have to think about 401K contributions for her. She did max out her traditional IRA, and in her last year looking to rollover all her IRA’s into a Roth and pay what looks like $0 in taxes.
I wouldn't be able to comment on whether you have no benefit from the complexity without knowing a lot more about your situation. It's easy for me to be an armchair quarterback and there are surely issues that I'm not privy to (such as the numbers

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