Re: Monty Hall, we have a PROBLEM
The total power you collect is just set by the size/shape/orientation/latitude of your device, which will be the same in both cases. Therefore, any difference in the rate of the temperature rise of your pool will be determined by the amount of power you *lose* out of the system - i.e. heat that leaks out in various ways. These would include conduction through your structure/supports, re-radiation from your collector, convection to the surrounding air, etc. All other things being equal, all of those mechanisms will allow more heat to leak out as the temperature of your collector increases. Therefore, your goal should be to keep the temperature as low as possible - seems a little counter-intuitive, but it's true. Therefore, you are better off running the two in parallel, so you get the same temperature rise across each one rather than adding the temperature rises together and creating a very "hot spot" at the outlet of the second unit. That will minimize the heat that leaks from the system and give you the faster temperature rise of the pool.
Unless, of course, running them in series means that your pump is working so hard that the extra energy it is putting into the system makes up for the additional heat loss...but heating the pool with electrical power is probably not what you had in mind!
Also, note that this is true regardless of whether the temperature rise of water with heat input is linear or not. As with most substances, the specific heat of water increases with temperature, so it's not linear - adding 100J of energy to cold water will result in a bigger temperature rise than adding the same 100J to warmer water. Regardless, though, you've still added the same amount of heat, so it doesn't matter. If everything were perfectly insulated (so that the heat leakage effect I mentioned before doesn't come into play), then you'd still be adding 100J to your pool, and the temperature would rise exactly the same amount.