1. Yes, property tax is not part of the basis of the vehicle, it is tax paid.
2. Yes, the cost of the vehicle includes dealer fees, registration, etc.
3. If you made a gain from the insurance payout greater than your business basis, you have a taxable gain.
4. You chose to buy a more expensive vehicle, there is no requirement for the replacement vehicle. You can choose actual expenses or standard mileage the first year. If you choose actual expenses, you may claim the Section 179 deduction to deduct more of the expense, based on your income and business use. Once you take the sec 179 and actual expenses, you will need to continue taking them. If you sell it before depreciated, you may have to recapture the depreciation.
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