Estimating Repair Costs for Rehabbing/Wholesaling

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I have some real estate experience but I don't have any construction experience due to that and the current market I'm looking to get into wholesaling properties in CT. 

I'm wondering how I should calculate and break down the estimated repair costs and materials?

Does anyone suggest any software? 

Should we start finding contractors to work with?

Any advice or guidance would be greatly appreciated. Thank you!