good enough in five years?
I've really yet to work for a company that plans more than maybe a year two in advance (some set broad goals that may stretch out a bit further but little actual planning - this experience goes back just about 20 years now across almost 10 companies).
The landscape changes so much it doesn't make sense to ask those sorts of questions in my opinion. New things come along that may change the way we approach stuff. I remember VMware once said that server virtualization was somewhat of an accident, not even they believed there was a market for it at the time and they were building the tech(I was a vmware 1.0.2 for linux customer back in 1999).
You also have to analyze the risk and return of automation. For some things it make sense, for others it does not. If it takes significantly more time to automate something than time saved then it makes more sense to not do it. Don't automate everything just because you can you'll be wasting your time.
I remember I interviewed some dumb shit for a director of operations role (the guy was interviewing to be my boss, NO IDEA how he got past the phone screening I think because he had met our then CIO at some conference). He was one dangerous guy. He wanted to automate everything, he wanted everything custom. He felt having our own data center was a "risk", because if I or other critical members of the team left who would be able to operate it? I didn't have the words at the time to give him the response because he kept shifting gears every 30 seconds(The IT manager was interviewing this guy with me and after about 10 minutes stopped asking questions because the responses were incomprehensible).
But in the end I would of said it's much easier for our company to continue operating in the event I leave the company than if you go and build some really complicated custom stack of shit that nobody knows how to use other than you because it's fully custom. With what we do we can go to our suppliers like VMware, like HP, etc and they would help our company (if we needed), or go to independent consultants, people can get up to speed very quickly because it's not obscenely customized and automated.
I told my CIO even before I started talking to this nut job that his resume had tons of red flags all over it. I later revised that statement to him the next morning, saying those were not red flags, they were land mines. Obviously he didn't progress past that interview.
Take some crazy automation custom stack and well you have to recruit someone to come in and read the code, and hopefully understand how stuff works. Not quick. Also hope they don't declare the system terrible and go on a expedition to re-write it.
I spent two years simply migrating a company from one bad implementation of CFengine to a good one(wasn't my full time responsibility and I was working in a "four nines" environment so I had to be careful). I am absolutely confident if my team quit the replacements would have a FAR harder time grasping what is going on inside of the Chef automation tool rather than the infrastructure components that are used as "utility computing" (not "cloud computing"). I can count the number of "system admins" that I know personally on one hand that would get up to speed quickly on fancy Chef stuff, yet alone any of the newer bleeding edge automation tool sets.
The more I see Trevor write, the less I feel he actually knows. It seems like he just gets briefings and talks to marketing people and lives on the hype machine. Having a little lab to play around with doesn't count as experience, I don't care what kind of workload you think you can generate, sorry it doesn't matter.