You will have several income documents to enter on your 2019 tax return. You enter the W-2 in Federal>Wages & Income, as usual.
For the Social Security Disability, you will receive a SSSA1099.
Do not try to enter your SSA1099 or RR1099RB as a W-2. Go to Federal> Wages & Income>>Retirement Plans and Social Security (SSA1099 and 1099RRB) to enter your SSA1099.
As for the other disability income, you should receive some sort of document in January for that--but not sure if it will be a 1099 or a W-2 since it is from a plan at work. You may need to post back at tax time for help with that one if it unclear then where to enter it.
Whether the disability income is taxable depends on who paid for the disability insurance,
Disability Income
https://ttlc.intuit.com/questions/1901145-is-disability-income-taxable
The medical expenses you have paid in 2019 can be entered as itemized deductions in the medical expense section, and you can include mileage for driving to and from medical appointments and procedures as a medical expense in that section. The interview screens will guide you to enter your mileage.
MEDICAL EXPENSES
The medical expense deduction has to meet a rather large threshold before it can affect your return. The amount of medical (including dental, vision, etc.) expenses that will count toward itemization is the amount that is OVER 10% of your adjusted gross income. You should only enter the amount that you paid in 2019—do not include any amounts that were covered by insurance or that are still outstanding. Of course, your medical expenses plus your other itemized deductions still have to exceed your standard deduction before you will see a difference in your tax due or refund.
To enter your medical expenses go to Federal>Deductions and Credits>Medical>Medical Expenses
2019 Standard Deduction Amounts
Single $12,200 (+ $1650 65 or older)
Married Filing Separately $12,200 (+ $1650 if 65 or older)
Married Filing Jointly $24,400 (+ $1300 for each spouse 65 or older)
Head of Household $18,350 (+ $1650 for 65 or older)
**Disclaimer: Every effort has been made to offer the most correct information possible. The poster disclaims any legal responsibility for the accuracy of the information that is contained in this post.**
