You would want to enter all of your information into the program to determine whether your itemized deductions are greater than your standard deduction, in which case itemizing would be more beneficial to you. Based upon the information that you enter to the questions asked, the program will calculate the most beneficial tax outcome for you!
Your tax situation can change from year to year, so you want to make sure that you look at everything to make sure you take advantage of all applicable deductions and have the most beneficial outcome.
To answer the specifics of your question, you will report student loan interest, HSA, interest income, and dividend income whether you are itemizing deductions or not. You will not report the mortgage interest/property taxes paid on form 1098 if you are not itemizing. However, the mortgage interest and property taxes are generally what allows most taxpayers to itemize, and opens up numerous other deductions such as medical expenses, state sales/income tax, charitable contributions, casualty losses, and miscellaneous itemized deductions (to name a few) that you would not be deducting by taking the standard deduction.
For more information, please refer to IRS Tax Topic Number: 501 - "Should I Itemize?" at the following link:
https://www.irs.gov/taxtopics/tc501
