On my main save I have probably around 150 sims and have been playing it and doing saves since 2014. I have had no winners, but I play rotationally and forget to play most of the time.
On my scenario rotational save one of my first scenario’s I had my Sulani sim ( a young adult female with a chesp house on the water, under 20K ) play the lottery about the second day I played her, and she won a million dollars! She redecorated her small home a little for comfort and style, You would never know she’s a millionaire though….. but, she can vacation any time as she doesn’t have a 9-5 job yet. Once they Fix the For Rent lots where you can change them back from Residential Rental to other types of lots, and I start playing again, I think she will be my first legitimate ( non cheating ) landlord! ….lol. Unfortunately, she wasn’t playing the millionaire scenario….. lol.