I had two major role models who influenced my financial path. Both were somewhat transient, but made a big impact on my way of thinking.
When I was a teenager, I had the occasion to chat with the father of a family I babysat for. I don't recall why we got connected, but I asked alot of questions about his real estate holdings. He had a multi-use building on Highway 99 that I recall thinking of renting one of the upstairs apartments. That highway is busy and I felt it was unsafe. I recall asking him how he came to own multiple rentals. His story stuck with me. When he passed each of the two children got half, I think the man I babysat for got 3 million. In no more than 5 years both his kids had blown through the money and had nothing to show for it. Needless to say I was hugely disappointed in the son who I babysat for.
The second big influencer was at the Company I work for now. He was a Marcom manager but on the side he invested in stocks and belonged to an investing club. He did so well that he (quietly) bought his dream home on the waterfront in seattle with a dock for his boat. He paid cash. I think he sold his basic rambler, but perhaps he rents it instead. The next move he made was to quit, and later he called to give an update. He bought a 20 unit apartment building with cash and was rehabbing it with his dad, one unit at a time as they came vacant. He was loving his new life and had decided to do some freelance marketing work as well.
Neither of these men had situations I have followed exactly, but it was their stories they shared with me that led me many years later down the path of owning real estate. I do hope one day to talk to the second man. I am not in a hurry though as my FIRE date is looming and I'd like to surprise him with the fact that I am FIREd like he is...Won't he be surprised! I even think I will be FIREing at about his age when the time comes.
My parents and DHs parents were examples of what NOT to do. Not a one of them utilizes their money effectively at all. They make really silly decisions that are mostly emotion based. Things like, pay 7k for surgery for a beloved dog that has 2 years expected life span. Hoard 150k in the bank for years because they don't know how to invest it. Buy brand new cars (that is just plain wasteful if you ask me). Nothing horrible, but all the basic MMM rules are not followed by them at all.