2011 Cruise Control, mod to keep it "on"?

Yep. Which means that even if keeping the switch down would be ok in terms of the on/off state of the CC software, you couldn't actually use it.

 

Hahaha, well *maybe* (referring to your note on the possible logic).

Note that most button logic (in general) actually triggers on the "release" event. Of course, we don't know how they actually programmed this thing. BUT, I will suggest that because of the resistor network, chances are that it would actually HAVE to be release-triggered, since you need a little bit of time after the button is depressed in order for the voltage to stabilize.

 

I totally understand where you're coming from @ToyTrainGuy. That's one of the many little things my wife's 10 year old Accord had that my '15 Taco doesn't.
Also on the list: auto on/off headlights, auto up windows, outside temp readout, oil life monitor, roll down windows with key fob.
Those aren't making me look at Ridgelines (cringe) but would make me like my truck even more.

 

Some of those are pretty easy.
Oil life monitor, for instance, does nothing different than you do in your head -- monitors how far you've driven. If you install an Android head unit and $6 odb dongle, you could implement this entirely in software. You could even display it in several different forms, like "miles until next oil change", "miles since last oil change", "% oil life used up", "% oil life remaining".

auto on/off headlights could be controlled by a microcontroller with ambient light sensor. You'll need to have it turn ON the headlights when the light drops below one threshold, and OFF when it crosses above a DIFFERENT (higher) threshold. You will also want to add a bit of anti-hysteresis code to smooth out the light readings (average them over several seconds) so it doesn't spike and make your lights "flicker".

The control over windows could be a bit more of a challenge. You may be able to detect when the window has hit its limits by monitoring the voltage running to the motor. The voltage will drop when it becomes more loaded. Adding an appropriate size of resistor to the line running the motor can help to exaggerate this voltage change.

The part about the key fob may not work so easily, since your fob doesn't have such buttons. But maybe you could implement your own with software running on your smartphone. That same microcontroller that is controlling your headlights (and your cruise control) could be hooked up to a bluetooth receiver in order to receive commands related to windows, or other functions of the vehicle like lights and horns and... starter? and control/override the accessory power running your head unit to boot it up before you get to your car.

 

That's what I'm talking about! Now if you'll kindly insert yourself into the next Toyota board meeting and show them how simple these are, we'll be golden.

The Honda fob doesn't use an extra button, you just hold the unlock to roll down the windows.

 

Yeah...I'll just press the button when I want to use cruise. haha