Thank you for your Well thought out question!
Turbotax Premier will handle the rentals very well but for the self-employment income, I would recommend either the online self-employed or the desktop/download Home and business
You can add a Pro review to any tax return either in the online version or desktop version.
Since you have several tax returns to complete, I would recommend the Desktop CD or download Home and business. (this only works on Windows based computers. We do not have a Mac version as of yet). It includes 12 returns of income over $25000 and 8 returns for income below $25000.
The pro review is pay ONE price ($54.99) for the product and you can review all the returns in the desktop version. We just ask that you call in one at a time. (Unless a couple of course).
https://turbotax.intuit.ca/business-tax-software/home-business.jsp
