I agree with this. It's a kind offer from your friend, but really only useful if you're traveling in the low season. I'm the daughter of a (now retired) UA pilot and once I turned 22 and lost my dependent benefits, I have never even attempted to use a buddy pass. There's just too much uncertainty - you are the absolute lowest priority - and an advance discount economy ticket often doesn't cost much more than the cost of using the buddy pass and you have a guaranteed seat. You might save a little on airfare, but you could spend far more than your savings paying for an airport hotel day after day after not making it onto that day's flights. And buying a last minute ticket for a train or flight between whatever airport you make it to and your actual destination will also cut into your savings.

If you check out websites like secret flying, the flight deal and scott's cheap flights you will see a lot of flights to Europe in the $500 range in mid-late August on full service airlines (ie not Norwegian or Wow). I assume this is because American kids are starting school and demand goes way down, but keep in mind that Italy will still be quite crowded with European families as kids there aren't back in school until September.