Man, since when did you have to make an account to use this site? I've played it before and this definitely is a new addition. I just simply refuse to make accounts for every little game I spend 5 min playing on the internet.
It's been there for quite some time. I believe the street view API is really not cheap for them to use, and the accounts are there to enforce the time limitation.
I love Geoguessr but it has a distinct randomisation problem (certainly in the competitive pool) that it hasn't solved.
If you play regularly you'll begin to notice that around 1 in 10 cities are in fact Vienna.
I'm not sure how it chooses, I suspect it first picks a country, then picks a city.
Without weighting for population or other factors, you end up with a significant number of Taiwan, Singapore and Vienna, far more than their populations or areas should suggest.