> there is a lot of bureaucracy at play and the process is not easy to understand even when you have experts to ask

I’d be willing to bet the reason there is a lot of bureaucracy at play is At least in part because realtors wanted job security. Just like taxes staying complex because of lobbying from tax prep companies.

I'm a bit confused about the tax prep. There's tax prep companies and software in other countries, too, and the incentives seem pretty much the same?

Germany has pretty complicated taxes, but I think they don't seem to have the same tax prep lobbying?

(In Germany, the complicated taxes are partially there because whenever you change anything or remove a complication, some people who currently benefit from that weirdness come out and complain.)

Here in Singapore taxes are mercifully simple.