I agree with your overall point that things like housing, healthcare, and education are much more expensive today and are much more difficult to acquire, securely, on a median income. However, when you say things like "I absolutely need a $600 iPhone for any modern job", it comes across like out-of-touch whining. No, you do not need the latest iPhone for any modern job. You want the latest iPhone. You can get a very capable, brand new Android phone for around $100 bucks.
If part of your job is conveying status, bringing an Android to work conveys a completely different kind of status than an iPhone. It may not feel good, but that doesn't mean $600 for an iPhone, even when you can barely afford food/rent, is poorly spent.
Functionally you don't need a smartphone to do most work. And that's coming from someone who works with the devices at a major telecom...
Location. Location. Location.
1,480 sq. ft., $23,000 http://www.zillow.com/homedetails/113-Bernal-Ave-Hickman-KY-...
918 sq. ft., $18,000 http://www.zillow.com/homedetails/309-W-B-St-Ramona-KS-67475...
1,056 sq. ft., $24,999 http://www.zillow.com/homedetails/943-Wisconsin-Ave-Beloit-W...
1,134 sq. ft., $27,000 http://www.zillow.com/homedetails/4751-Bellm-Dr-SPC-20-Klama...
2,064 sq. ft., $28,500: http://www.zillow.com/homedetails/908-Lelia-St-Newport-AR/10...
Everyone else who's not in this small minority still has a right to complain about coastal/urban housing prices.
Well sorry, the exact same 1200 ft^2 brick home built in the 50s, that you bought for 2 year's salary (with a high school education) in the 70's, NOW costs 6 times my salary (or 12 times the median salary for the area).
The $600 iPhone which I absolutely need for any modern job (thanks to BYOD) isn't gonna make a dent in the cost of housing, health care, and college these days.