In fact, I will admit I’ve made plenty of mistakes around personal finance, business decisions, real estate decisions, and even in my own marriage.

@Rob MassopustI agree with what you pointed out about making an informed decision and knowing what your personal strengths and needs are when picking a broker.

For that you must gain clarity from your 'pro' team members knowledge and decisions of what can and will be done, by whom, at what costs and over what timeline. 

Most good contractors have experience in current building codes and have made adjustments with the current codes to keep their costs down.I speak from about 30 years of construction decisions in the Dallas Texas area. 

I’m new to Real estate and have an opportunity to buy a duplex for 440,000 in the local dallas area but before I make any decisions I wanted to know the best way to break a deal down so I can create cash flow

Should I look to calculate the depreciation savings on the property when making a decision? 

But now that I'm working on my 2019 tax return and revisiting the cost basis I did for 2018, I feel like it was done incorrectly.

Real estate, more than anything else I've done, demands that you make quick high-stakes decisions on the basis of information that is always incomplete.You've got to be able to pull the trigger.

They have been educated at that point and will make their own decision on how to proceed.

What you've got to do is adjust expectations and make the decisions now that maximize your benefit.