Every company and every jock is a different situation - the gentlemen with the well worn Koss headphones (cranked to 11

) you speak of is a pro and one of the best jocks on the air. Period. I'll find his Z100 video aircheck on youtube and just sit in awe of the ability to be entertaining like that, and I hope someday I can be half as good. A great jock is a great jock - but I think Mr. Tiller is lamenting the fact that great jocks are getting fewer and fewer on the dial, largely in part due to cutbacks.
While the financial cuts that radio has gone thru may not have hurt his ability to be entertaining, I have an example where a full timer down the hall was replaced by a part timer (this guy did a drive time shift and was APD/MD), and the quality of the product hasn't been the same since. Many places have 1 person doing double duty, or triple duty, for the same salary just to hang on to a job. How many PD's oversee multiple stations where years ago they just oversaw one? While this does not immediately lead to a poor product, over time the cumulative (no pun intended) leads to the weakening of the brand and employees that are burnt out and doing their best to tread water. The worst part of deregulating radio was the dark side of taking on all that debt to buy properties - firing people to make the bottom line look better and worrying about the consequences later.
I will say Cox is one of the better outfits - I have a friend who works for Cox on Long Island, and has nothing but great things to say about it. They treat him well, and have grown him along to be a promising air personality and talented at skills ranging from production to scheduling music. I have also heard from others who didn't have a great experience with the company, but not everyone will have a great experience for various reasons.
It seems that the companies that never took on great amounts of debt (Cox & Greater Media to name two) are better to work for than publicly held companies that have to appease investors rather than advertisers or listeners. But when all the large groups start voicetracking and consolidating duties and jobs en mass...well, it signals that it is ok for everyone else to do the same.
The tide seems to be turning back to local programming and investing in talent - stations near me have re-instituted live shifts where they were tracked before, and have dumped satellite programming to go local. Hopefully more will do the same - after all...have to have some training ground for the next generation of personalities.