Knowledge and expertise in what you're looking to do specifically.

You have to complete Schedule E if you have rentals.You should check if the turbo tax premier version allows the filing of Schedule E.With that said, using a software like Turbo Tax will assume you to understand what is deductible.If you work with a tax professional, you are more likely to have an accurate return.

Quote from @Mike Hansen: When out of state investing, how does one go about appealing their tax assessment?

Filling out the contract etc. is not that difficult but without being active in the market every day and having expertise that comes from doing deals all the time, beginner mistakes like this are going to be made and money is going to be left on the table every time.

Example 1 - I used to have extensive expertise of automotive repair facilities located in Harris County, Texas.  

Allocate equity based on contributions: you provide the $235K HELOC and management, while your former boss contributes renovation expertise and labor.

The 1031 exchange is what allows them to do this without having to pay tax on the gain or depreciation recapture. 

Tenant issues are more likely to arise and then you have the owner....many aren't qualified expertise wise or financially to weather the storm.

Wherever you have a subject matter expertise.

-Transfer the property into an LLC – This may allow me to take ownership while potentially avoiding property tax reassessment, however this sounds like an involved process-Establish a living trust for my aunt and mother – The trust would specify that I inherit the property upon their passing and provide step up in cost basis but i'm worried that the living trust can be modified to have me removed (who knows what can happen) - My mother is somewhat volatile.I would like to live in the property and my mother will live in her second property with her husband.