Timer causing error on "Cancel"

That’s bad syntax, you’d use double == for testing equal.
However, better to use != OFF for not-off. It’s not quite the same effect, as it will still work as desired if the Item happened to start out as NULL

Use hysteresis! Even mechanical thermostats include that, a “dead zone” where no change is commanded, the system is left to continue doing what it was doing. It stops the system rattling from one state to the other.
e.g.
> 18.2 or < 17.8 gives you 0.4 degrees of hysteresis

Thanks – I have implemented that change in the previous “rule” which I currently have commented out. But in theory, based on where @rossko57 is leading me (I think), I probably won’t need the timer?

I’m not sure what hysteresis is, but sounds like you’re recommending it – and I’m definitely leaning on recommendations right now!

How about this;

rule "Its Hot Detection - v31782636289698"
when
    Item TadoFamilyRoom_Temperature changed
then
    if (TadoFamilyRoom_Temperature.state >= 18.25 | "°C" && ItsHotTemperature.state != ON) {
            logInfo("EXTRA", "Family Room Temperature is high ("+TadoFamilyRoom_Temperature.state+"), the It's Hot toggle switch is now ON")
            pushNotification("Temperature", "Breached threshold, It's Hot toggle is ON -- tado should be OFF/Manual")
            ItsHotTemperature.sendCommand(ON)
	} else if (TadoFamilyRoom_Temperature.state <= 17.75 | "°C" && ItsHotTemperature.state != OFF) {
        	logInfo("EXTRA", "Family Room Temperature has dropped ("+TadoFamilyRoom_Temperature.state+"), It's Hot toggle switch is now OFF")
            pushNotification("Temperature", "Dropped below threshold, It's Hot toggle is OFF -- tado should be ON/Scheduled")
       		ItsHotTemperature.sendCommand(OFF)
    }
end

Well, introducing hysteresis slows things down by using the thermal inertia of the real world system.
In your example there, if live temp is say 18.0 then the heating/valves/whatever are left to continue doing what they were doing before. If it was heating, it continues heating until 18.25. Then it is allowed to cool down to 17.75. The cycle gently hovers between these temps.

You may still want timing elements to do with your notifications or to do with this manual override you mentioned?
Basics first though.

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Happy for Notifications to vanish – they were purely in place to check the rule(s) working.

Manual override would never need to be a thing - in theory. Though I’m comfortable in setting Setpoint rules etc…

I’m just looking to get the basic on off, based on temp working. I can play from there.

I’m a fair weather openhab’er, I go weeks/months/years without tinkering, and then when I do, I found the system has changed, or any knowledge I have has completely vanished. Usually, a few hours in to it, and I can pick things up again, but this one has me stumped!

Admittedly, childcare & browsing on my phone hasn’t helped me absorb stuff this time around!