That's great if you are near a large city like San Francisco.
However, Madison, WI <-> Milan, May 7 - May 20, United: $1304 economy, 21h travel time.
It IS the $2000 airfare ( or approaching it).
Now, ORD <-> MIL is $687, but MSN -> ORD is at least a 2 1/2 hour trip by car, longer by bus.
It's a $60/rt ride from Madison to O'Hare on the Van Galder bus. If you drive, it's whatever cost to take your car plus at least $10/day at ORD.
I used to pay ~$1500 CAD from Ottawa, Canada to Manila, Philippines. Now that I’m aware of deals and have a flexible schedule/remote-work-policy I scoff at any trip with the same itinerary that’s > $800.
A lot of folks, however, aren't comfortable with putting themselves out there into an airbnb (or equivalent) and fending for themselves with local markets and transport. It's really not that hard (depending on where you go and your tolerance for embarrassment and alienation), but there's definitely a language and cultural barrier that needs to be overcome or worked around.
I think that Rick Steves, in his unique way, makes a lot of people feel more comfortable with getting out there. It really is so much better to travel without a tour company mediating the experience.
It's also not hard to get by in most places in Europe, particularly Scandanavia. Most folks there speak English, among other languages.
For example:
San Francisco <-> Milan, May 7 - May 20, Norwegian Air+Easy Jet: $598.
Air Bnb for the duration: Central Loft, $70/night, 13 nights, $910. (you can find much lower as well, if you want to go for the minimum).
Shop local, cook & eat in the apartment, $20/day? $280.
Spend 13 days walking and exploring Milan for under $2,000.
That's not a trivial amount, but it's not the $2,000 air fare and $150 night hotel and $50 day food type of money, either.