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упёртый - word with negative connotation for stubborn, pursuit of one's goal
the expression is Упёртый, как баран = Stubborn as a ram (meaning is negative, ram being a symbol of stubborn stupidity...

not necessarily, it's a humorous metaphorical description (but the connotation is not very positive), but could be an insult if used in a certain manner...
also you are perfectly right when you say...

Antonio,
This 'humour' reminds me of 'office bottom dweller' discussion I started in 2011 http://masterrussian.net/f31/office-plankton-18414/

Mordan,
The idea behind this is an average office worker stuck in tedious and boring office routine. It's warm and relaxing somewhere (Maldives in this case), but you have tedious work to do, so...