Do I need to buy the software each year or once I have it it will automatically update every year to their respective version?
You buy it every year. It's still cheaper than an accountant. I buy the one that includes a state tax program (I'm in NY). It cost a little more.
Basic is free to use on line, but that's only for the simplest tax situation.
Deluxe is good for those who have deductions. Good for most people here.
Premier if you have investments like stocks or rental property.
For a business 'schedule c', I think you need the 'Home and Business'.
'Business' not 'Home and Business' for a trust. Can't get one that includes state taxes.