Two things. First was agreeing to let DH "invest half" of the stock I'd received when leaving a biotech start up in CA. NEVER should have done that. I had no idea of how the stock market worked and he kept buying on margin, because his "half" was worth more as the market climbed. I'm an idiot... should have made him move "his half" to a separate account. If he'd left it alone, I could have sold it for $80K (initial investment $1200), but at that point he owed about $60K on margin. When the stock market tanked, we sold it for barely enough to keep from losing everything. I almost divorced him- seriously, and I told him if he EVER dabbles again, I WILL be GONE. So far, so good... that was 16 years ago and our only connection with the stock market is whatever TIAA/CREF is doing with our retirement.
Second... My mom owned a cottage-type house on the coast of Maine. It had a LOT wrong with it, it was owned by the family trust when mom died, the 4 kids were happy to keep it there and rent out the top floor w/my brother living in the bottom apartment. We probably owed about $12K on the mortgage (at 11%
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). Anyhow, 2 of us lived out of state and the 2 who were there in town were over being landlords, and the house really needed work, and nobody had any money. My brother moved in with my sister&BIL (BIG sea captain's home, plenty of space for everyone to come vacation,etc.). You can see how this is going to go. We sold mom's home and each cleared about $50K, which was nice to make improvements here at home, put towards retirement, do some special things for DD, purchase her a used car, etc. Within a year, my BIL left my sister and the kids, partly because he'd finagled them into terrible financial state and it was all coming apart. They lost the house, BIL is gone, sis, 2 kids, and brother now live in a 2br apartment. What really eats at me is that at the time, I had no idea of how home equity loans work. We could have swung $50K easily, fixed up the house, and my bro and sis and the kids would have had a place to live. I know it was an incredibly stupid decision to sell now, but at the time, I just couldn't see how financially it would have worked out. I kick myself every time I drive by in the summer and see the upstairs rented out at $1500 a week, downstairs at $900. Sigh. I'm the oldest, I had the best/most credit, and still feel that I somehow should have made it happen for us. But no...
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