DYI for big ticket home maintenance items

I’ve gotten quotes for various big ticket maintenance on my home such as painting the outside of the house, putting on a new roof, and restaining the deck. I’ve been blown away by the bids I received!  A general contractor friend told me that he is astounded by how much he can charge on projects and have people still beg him to do the work.  He also mentioned that insurance is a significant piece of his cost structure and that for certain sub-contractors like roofing, can equal the cost of labor! 

I started to look into doing the work myself like my dad did back in the day.  Because the quotes are so high, it looks like I could actually buy scaffolding, materials and specialized tools for the work, for a small fraction of the bid costs!  I wanted to hear from anyone who has done their own work on bigger projects and which projects they actually did the work themselves and which project they avoided and why.  

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