Maybe you don't understand what I'm worried about! I don't worry about putting 2000w in an outlet but if I were to plug in two 1000w lamps I would obviously have to use a multi-socket or power strip to run them on the same timer. I am not saying it is impossible or crazy to plug a fucking outlet but I am saying that I would rather not plug the timer, a multi outlet and the two lamps into the same outlet since the power has to be backed up first by the multi outlet, then to the timer and finally to the outlet. It would be so easy to overload one of the three and cause a fire.
A timer has a rated current, most in Aus are 10 amps which will handle at max 3 600watts lights or 2 1000 watt lights, so long as the load is under the timers 10 amp rating there wont be a problem with the timer, the thing with lighting is the startup uses more amps and then lowers to its continual use flow of current, this startup can overload the circuit, lots of modern lights have a staggered startup to address this when lights are multi ganged on one circuit.
Now when the lights first start up they use more amperage and can overload the timer, or the multi-plug board, or the main circuit breaker, all these parts have rated amps, no matter what the configuration the rule is don't go over the lowest rated item along the entire circuit.
With timers the biggest risk of breakdown is the startup where the initial surge of power is highest, this is why you run a contactor between the timer and the appliance.
A single timer and contactor can be used to power on/of any number of lights, so long as the lights are split onto different feed circuits so the lights don't overload the main breakers. like you could pull the lighting power from 4 different circuits that have 2 or 3 lights on each, the single timer and contactor would control them all. The timer is only turning the contactor on/off there is no high current going through the timer its going through the contactor in that situation you would use a 4 pole contactor which means you have 4 feeds going in to the contactor and 4 feeds going out, its all just a matter of adding up your current draw in watts and splitting that across your circuit limitations, plugs, timers, multi plug boards, double adaptors etc, each have a rated max amps, and the lowest rating is your limitation on any single circuit, if you want to run a lot of things you need to spread the load across many circuits by either drawing from different power points around the house that go back to a different breaker in your main power box on the side of the house, or by running a heavy cable to the main power box connecting to main supply line on a 60amp breaker and then split that into say 6 x 10amp plugs inside the room.