One major problem I see with all recent "upselling" trend on WordPress is the price structure, particularly the trend towards yearly subscriptions.

Whilst I recognise the economic reasoning from authors the current prices exacerbate an economic divide! Yes, I understand that if you live in California or central Europe you need a minimum income as a WordPress developer. But current pricing trends have moved WordPress out of reach for poorer people.

Prices that average US$50 (or more) per item might be fine for users from wealthy countries, but they make it near impossible for a low budget start-up from a poorer nation to set up any successful website with WordPress.

Usually it's not one premium product one needs to set up a site, but a whole basket of these: premium theme, several premium plugins (from contact form to features missing in the theme to possible image optimisation, etc.), premium caching, and more. That's all before the annual hosting bill!

So starting a WordPress site might require an upfront and repeated annual investment of easily US$3-400/year = which equals the minimum monthly income in many countries, even in Eastern Europe.

So the premium add-ons move the so-called free WordPress out of reach for too many!