I reckon flipping houses and renovating is one way - Buy an older house. Spend dodgy money into some serious renovations. Sell house for <original price> + <cost of renovation>. Money washed.
I think complexity here is migration to Python 3. Seems like the author picked Django and Python 2 in 2011. Python 3 was released in 2008. So by 2011 should have been clear that you might be facing a migration project sometime in future. Having made that choice getting 8 years out of Py 2 is pretty good. (Not saying he made the wrong choice. Would have made the same choice myself.)
Seems he would have done very well out of property as Australia hasn't been affected by 2008 GFC. There are young people that would have invested in property in Ireland before GFC and would have dug themselves a financial hole. This guy doesn't like calling it luck but I don't know what you call different outcomes for investors between the two countries. We are living in the time of quantitative easing, cheap credit and this seems to result in speculative asset bubbles and busts. Dow Jones is over 200% up in last 10 years. I think outcome of central banks printing money at this scale is unknown and puts a big question mark on long term investing and the 'time in the market' advice.
DJIA-30 has risen from ~9000 in early Jan of 2009 to ~24000 now, a gain of ~167%.
That is a CAGR of only 10.3%, which is fairly inline with historical price appreciation of the S&P-500 index (10% total return and ~8% price appreciation). To damp out some of the short-term gyrations, taking the same index and average close prices for all of 2018 vs all of 2008, implies a CAGR of 10.9%.
The S&P-500 index is more representative of the overall large cap market than the DJIA-30, IMO. That index is up ~200% in 10 years, for a CAGR of 11.5%.
These returns are not stratospherically higher than historic norms.
In a printing money environment (which I am similarly concerned about), you want to be invested in something other than money. Real estate and equities are hedges against deflating money. (Gold bugs would argue that precious metals are as well.)
