It's almost always a lack of will to spend the money required or accept the pain necessary and NOT technical feasibility. If you build your systems to the strictest of standards or beyond, then you are by default in compliance with the rest.
Doing things "right" almost always gets hamstrung by the dollar figures required or by "business" push-back. "Do we really need to install IDS/IPS equipment in every little branch network we have?" Yes, yes you do if you want to prevent and catch breaches early. "What do you mean I shouldn't use my iPad pool-side while on vacation to do my work? I'm the CEO." Yes, but that guy taking pictures of your screen behind you on the balcony isn't and the guy that's going to steal your iPad while it's unlocked when you get up to get your margarita certainly isn't.