The Anecdote: In 1929, during the height of the bull market, Kennedy was getting his shoes shined when the young boy shining his shoes began offering him stock tips and discussing the market with confidence.The Realization: Kennedy reasoned that if a shoeshine boy had an opinion on stocks, the market had become dangerously popular and saturated with inexperienced investors.The Action: He supposedly decided to sell off his significant stock holdings shortly before the Black Tuesday crash in October 1929, thus preserving his family's fortune and profiting from the subsequent decline.

Stock futures extended gains, reflecting investor expectations that the Federal Reserve will hold rates steady at its December meeting.

The stock market fell down today, for example.

As for Philadelphia, where I am from, you’re going to face older housing stock, more regulatory complexity, and neighborhood-by-neighborhood variability, manageable, but not ideal when starting out.Once you build equity and confidence, you can diversify into other markets.

Having someone who understands timelines, budgeting, and the realities of construction on the ground is invaluable, especially here in the Twin Cities where older housing stock can throw curveballs.I work with a lot of local investors on fix-and-flip and value-add projects, and the deals that go the smoothest are always the ones with a builder-minded approach like you described — clear scopes, aligned expectations, and honest communication from day one.

I think $1,500,000 is a decent retirement savings where you don't have to go crazy and live a decent lifestyle.If you can make 6% to 8% annually, hopefully you can rely on $20,000 - $30,000+ of social security benefits which gives you $100,000+ of annual income.If you find your money getting stretched, sell the house, and put the net proceeds into the stock market / real estate and then rent something.

This post is more of a question about the stock market.

I wouldn't have borrowed money to put into the stock market as the bulk of my net worth was already in stocks, so it was kind of a diversification play...and I wanted to see if I could make money not using any of my money...since the HELOC was revolving credit.I learned that I won't ever buy a rental house in my state again. 

A CPA might look at doing a cost segregation to accelerate depreciation, an installment sale to spread the gains over time, or structuring the sale as an asset versus stock sale to reduce taxes.

Don’t skip the rent comps just because it’s new construction.Appraisers will still use nearby rental stock.