I think you and the person you're responding to are dealing in absolutes. In some ways it is harder, but in others it's easier. The world's knowledge is literally at people's fingertips now. Almost any creative skill someone has can be leveraged to make money. In many ways it's the easiest it's ever been to start a business or make money.
But, as you mention, homes are priced insanely high. The flight to the coasts has caused anything within 50-100 miles of the ocean to go crazy price wise. That is much harder on people.
Healthcare is a mess. One of the biggest small business unlocks the US gov. could do is pass universal healthcare. So many people are tied to companies for healthcare, and boom we would see if we could break that tie would be like the tech boom all over again, if not greater.