This is neat. Although I'd really like it to change the "lol sure" for some other thing when the weather is really nasty.. e.g. "LOL SURE, CAN YOU HANDLE -12ºC AND FAIR WEATHER? OH, 82% HUMIDITY AND 23KM/H WINDS TOO"... (when I searched Moscow).

If it is a possibility to get the average conditions on the place, you could define some thresholds to determine the 'advice' and thus answer the actual question of 'can i leave?' :)