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Are you a younger person? Unfortunately, contractors know when they can take advantage of someone based on the questions you ask. A lot just comes with experience. I learned a lot just by doing side jobs with my dad growing up
Start doing the work yourself like your dad and his dad did.
Coach
Experience.
Breakdown the quote into materials and labor and estimated hours to better sanity check ot
Another option is to work in like property management, development, and/or construction. You could probably also volunteer for like Habitat for Humanity, so something like that. I don’t personally know how to do any construction work and have no one in my family that has worked in a trade, but I’ve worked in commercial property management so I’ve been exposed to a lot of building development, building out of tenant spaces, maintenance and repairs on buildings, etc.
You just have to get exposure in those areas so you can learn what it really takes and how much things really cost.