All of your Medicare and your Medigap premiums for the months that you are self-employed are deductible as Self-Employed Health Insurance. You can deduct them in the Business Expense section under Other Common Business Expenses>>Insurance Payments>>Health Insurance Premiums.
Your workers comp would be deductible as business insurance as would any liability insurance you carry. This would again be under Other Common Business Expenses>> Insurance Payments>>Business Insurance
Yes, you would be able to deduct the cost of your replacement tools as a Miscellaneous Expense (assuming these are small hand or power tools and such and not something like a $10,000 scan tool). The Miscellaneous Expenses are also under Other Common Business Expenses. You will just enter the description and amount.
If these would be large or expensive tools such as a scanner that cost $10,000, you would enter these under depreciable business assets. Then you would walk through the steps to either take a section 179 deduction or to take a depreciation deduction.
Business Tax Deductions
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