I grew up in a household where thrift shopping and penny-pinching was a necessity. Dad's plan for financial independence was via real estate. He felt that he could claw his way up the ladder by buying the worst house in the street, renovating, then moving on to the next, over and over again. The reality was that life tends to get in the way of the best-laid plans. What he did achieve was a rental that covered the repayments, and at retirement age, they sold it. End result: one family home paid off but in need of total renovation (aka, land value), and an apartment sold & invested into their retirement savings. Keep in mind, this is already beyond what the average family ever achieves! My dad is still working part-time, but it's not my dream to be still working at almost 70. I'm too precious for that. Read: lazy.
The first home I bought was when I was a young single mum, and it was a relocatable home in a caravan park. Although I never made money out of it, it worked out slightly cheaper than renting.
Once I had a full-time job I took out my own loan for a small holiday house in the country. There were no real investment plans behind the decision, just a leg into the property ladder for us. After a few years we moved into it ourselves.
I also lost all real enthusiasm for DIY once I was living in it. Apart from a bathroom and garden spruce up, it was pretty much sold as-is five years later. It didn't make me any money and only just cleared the total debts to my name. What did I learn? I'm completely capable of doing umpteen handyman necessary things around the house, but they're not my passion.
That sale was at the time I moved to Finland to marry my husband. And I buried my real estate plans to start a new career as a... well I wasn't sure yet, but it was going to be something conventional. Buahahaha! (Yeah, sure.)