How a thread can go to three pages, when post 2 could have been NO and done... amazing.

Despite being fully capable of pressing the "power" button on the locally placed cable boxes, he doesn't want to have to do that.

From my understanding the client doesn't want to get off his @$$ in his $10K chair, however if you force him to press a button on the remote he may be more receptive to this solution.

I had a client once who fit your description very closely. The added detail is that he lived in a wheelchair and getting his ass off his $10K chair was not trivial.

If he's handicapped, or rich, what's wrong with making money by serving his need? Why the resentment?

I have one of these types too, along with some visual and cognitive impairment. The control system is a major quality of life improvement.

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I like this one! Toslink output would be a reliable light source for the right sensor. As far as I can remember, the optical light is off when the soft power is off (box is in standby).

This is a great way to go. It might take more time to program, but it could also educate and empower the user as they troubleshoot.

Which Crestron Remote?

You asked using the word "any," right?

You can get yourself discrete on and off of any device by adding one of those one-circuit RF remote on/off power switches, the kind they sell during the Christmas season, and that I've also often seen at Home Depot at pretty much any time during the year.

It's not RF. It won't learn.

Here's a detail that might not be in people's thoughts, since nobody has mentioned it.

When the unit is turned off, it will not be able to download automatic updates. And, when you turn it on, it will have to boot.

But it does what is asked of it.

So I had a customer who was rich and lazy and didn't want to get out of his bed to press anything or plug something in so everything kind of had to be within reach of the bed or controllable from a remote.
So my task was to make some wireless headphones cut out the sound from the surround sound receiver to the ceiling speakers when they were active but being that the source of audio was from the headphone jack on the surround reciever located in a closet that required walking, it was too incovenient of them to plug the 1/4" plug in each time to the headphone jack and leaving it in would result in the sound not working on the ceiling speakers. So I hacked the surround sound receiver and modified the headphone jack's switch that detects when plug is in and routed that to a relay that I could remotely control that I mounted in the surround receiver. I made a custom cable that I ran under the house going from the receiver to a wall jack by the clients bed. Two wires for relay coil, Three shielded wires for Left, Right and Signal ground. I also hacked the base of the wireless headphones as there was a green LED that would light up when the headphones were removed from base and active. The green LED was controlled by an output pin of a processor in the Base unit. I tapped into that line with a resistor ran it into an optoisolator whose output I then ran into a transistor with a 12V output to trigger the relay inside the surround receiver and trick it into thinking the headphone plug has just been plugged in even though it was plugged in the whole time.
So the point is, with a little modification to the cable box, assuming there is an LED that lights up only when the box is powered on or some other kind of logic output you can find when it's powered up, you can utilize that trigger something else. Usually the boxes even when powered off, will have some kind of standby power like 5V DC you can use to power a monitoring circuit. So if monitoring the Power LED and circuit detects it off, it can trigger a delay which when timing out triggers a relay with contacts feeding to the power button on the box which would be as if someone went up and pressed the power button on the box.
This maybe a little complicated, but can be done. I've done this trick many times..

Have you had any trouble with cable box firmware updates or the cable company mandating a box replacement?

For example I used the cable box switched outlet for many years, but they have all been disabled or eliminated at this point.

Xantech's CC12 (one DPDT relay on a chassis) or CC62 (six DPDT relays on a chassis, if they still exist, are IR controllable DPDT relays that will let you do all sorts of things like what you did.

Years ago I worked out that an amp's headphone output is generally a power amp channel's output fed through a 300 ohm or so resistor (one per channel, natch) to keep from blowing up headphones, so you could take the power amp out and route it directly to speakers, then switch it to headphones through the resistor. No need to open the receiver.

In fact, opening the receiver means that any time that component needs service it needs some custom care. The above-suggested relays let you do what you need without having to modify the receiver in any way.

Yes, cable boxes always have something in them like five volts... to make the IR sensor work.

So I guess the problem kind of lies with customers who are rich and have money and those that are older. The rich ones feel they don't need to put any effort into learning anything or dealing with any issues as they can just pay someone else to do that. They feel they can just throw money at it and it should work to their expectations even if there are limitations due to poor engineering on the manufacturere's part. Then the older customers are just not savvy and are easily overwhelmed by the slightest tech challenges. To me, it's a waste of my time for me to drive out to a location where they claim "The TV in the office is not working" and then when I arrive, the TV is on a channel number as if there is an antenna connected rather then HDMI 1. So I change the input to HDMI 1 and they are happy again. So I guess there is no way to make a system foolproof for every type of customer/client.

Upgrade them to DirecTV IP controlled receivers and control system.
But we have many projects that use Cable Boxes as well, and just don't have this issue. Maybe they need to be used (keep alive) more frequently.

I would issue an IR PowerOn command in the AM...ready for use during the day.