Paging @Dicey who has done house flips.
Thanks, former player. I saw this thread yesterday and wanted to ponder on it a bit... Since DH is the mastermind of our operation, I've been thinking about how he acquired his skills. Settle in, there's a Dicey story coming...(There's a TL;DR at the bottom.)
When he was in his early teens, his parents bought land in an upscale community and built an elevated *round* house. The infrastructure was steel. I recently found a picture of DH and his dad. In it, a young DH was on the ground welding, glistening with sweat, and his dad was casually sitting on the welder, watching him, which was pretty funny. They built and finished the house themselves and the family moved in.*
DH was always mechanically inclined, starting with bicycles, then mini-bikes and go-carts, then motorcycles, then cars, boats, etc. Fun fact #1, from his freshman year, he rode his motorcycle to the first and every day of his new high school. He said he always wore a full face helmut and parked behind the school where the teachers parked their motorcycles. Since students typically arrive after and depart before teachers, apparently nobody ever caught on.
He graduated, went to college for a year or so, but wasn't really into it. He started painting houses and earning very good money, so he finished up his classes and and opened a house painting business. He was later offered a job in a national chain paint store, and became a manager for several years. He then got lured away by a major painting contractor (Fun fact #2: he painted all the Noah's Bagels in NorCal, and several new Walmarts), then another, then went back out on his own. Eventually, he sold himself and his skills to a public utility, in exchange for sweet benefits and nice retirement package. He got to paint really big things and naturally, kept painting houses on the side.
Along the way, he married his high school sweetheart, bought a house and started a family. Their house was an older starter home, and his FIL was into flipping houses. They worked on DH's house and then DH started working on FIL's other projects on the side. He liked his FIL and helped him out for years. I'd say that's where he learned a lot of his DIY skills. He is also whip-smart and can teach himself anything. He has a love/hate relationship with YouTube. He learns a lot there, but hates it when people post stuff that's just plain wrong. He's also a whiz at digesting dense technical manuals. His reading comprehension is off the charts.
I had acquired my own DIY skills through sheer economic necessity. After
years of always being a broke homeowner, I decided to hire a painting contractor for my most recent fixer house, because it was two story and had some crazy tall ceilings. I had to be away on business when the house was ready to be painted. DH was a friend of a friend, and a licensed contractor, who preferred to paint empty houses. Because it was his side gig, his overhead was low and his price fit my shoestring budget. I returned to a beautifully painted house, and happily moved in.
A decade later, when I decided to recarpet and paint my house, I knew who to call. By then, he was a widower with two young adult kids. Unexpectedly, sparks flew and we married after a whirlwind courtship.
Shortly after we wed, his dad died and we realized his mom had Alzheimer's so we knew we had to figure out different living arrangements. In short order, we fixed up/packed up/sold three houses, and bought another. It was a new-ish, custom built clown house, but the builder ran out of money and scrimped on some things near the end, so it needed a bit of work, too. Later, we bought two more houses where I already had a rental. We fixed them up, and rented them out.
Because we couldn't travel, we were looking for another local project. A realtor friend found a house that needed work, so we bought it, fixed it up for fun and sold it for a nice profit. Couple years later, she found a worse one and we did it again. Then the market went nuts and nothing has made sense since, so we're back to working on our primary home.
And that's how we acquired our DIY/flipping skills. My first thought when reading this thread yesterday was, "Hell NO!". Upon reflection, to a certain extent, that's kind of how we got where we are. There a million degrees of DIY and many ways to learn.
TL;DR - OP: If you decide to go this route, speak extensively with your friend. Spell things out and put them in writing! Make sure he has insurance, and get proof of coverage. My brother had an interlude between jobs and agreed to help out a contractor friend. Dude swore he had Worker's Comp Insurance. When my brother fell off a roof and broke his pelvis, he learned some very hard life lessons. Learn from his mistake.
*When DH's parents eventually sold the round house, the new owners built a conventional house on the other side of the property and converted the round house into an artist's studio. They landscaped heavily around the round house, and it's no longer visible unless you know exactly where to look. I'm sure the rest of the community prefers it that way.