Highway Use Tax on federal return

Which state?  Is this for business or personal  use?

If this is a business vehicle then you can deduct it as a business vehicle expense.  If you are taking the actual vehicle expenses instead of the standard mileage. 

If this is a personal vehicle then probably not.  The Highway Use Tax is likely a fee similar to vehicle registration and that is NOT based on the vehicle value, meaning if you paid $50,000 it wasn't based on the $50,000 it was based on the class of vehicle you purchased or the weight or something other than the cash value of your vehicle.  If this is the case, then it is not a deductible expense. 

The rest of your sale tax IF you are itemizing can be entered as a major purchase, however, state and local taxes are limited to $10,000. 

Itemized expenses include mortgage interest, state and local taxes up to $10,000, medical expenses in excess of 7.5% of your AGI and casualty and losses in excess of 10% of you AGI with the first $100 not counting towards the loss.  Your health insurance and all medical expenses are only deductible for the amount that is over 7.5% of your AGI.  This means if your AGI is $50,000, then the amount that is over $3,750 is deductible.  

Then your total itemized expenses would need to be greater than your standard deduction below in order to benefit from your insurance premium payments. 

The 2023 Standard Deductions are as follows:

• Married Filing Joint (MFJ)              $27,700
• Married Filing Separate (MFS)      $13,850
• Head of Household (HOH)             $20,800 
• Single                                                     $13,850                                

Blind and MFJ or MFS add $1,500

Single or HOH if blind add $1,850

Deducting Auto Expenses

Is Your Car Registration Deductible?