You are using a Y splitter for output 2 (timing ref) which is where you made your mistake. The idea behind loopback timing measurements is to compare the time between two circuits.
Set up your
Focusrite 2i2 like this:
CIRCUIT 1 (Measurement circuit):
OUTPUT 1 ---> to your amp, speakers, etc.
INPUT 1 <--- Microphone
CIRCUIT 2 (Timing reference circuit):
OUTPUT 2 ---> physical loopback cable ---> INPUT 2
Now set up
REW like this:
Mode: ASIO
Output device: Focusrite 2i2
Output: OUTPUT 1
Input device: INPUT 1
Timing reference output: R (assuming output 2 = R)
Loopback input: R (assuming input 2 = R)
Question 1: If you are using REW's "measure" function, REW sends a chirp through the loopback reference circuit. I believe it's the same tweeter chirp that is used if you use an acoustic timing reference. Other types of REW measurements allow you to send different signals through the loopback circuit, for e.g. if you use
time alignment with wavelets REW will send a wavelet through the loopback timing reference circuit.
Re: measuring through the Wiim Ultra. The problem is, you have only one output from your Focusrite, and two inputs (L/R) on your Wiim Ultra. Your options are (1) measure L and R separately, which will mean recabling between measurements or (2) use your Y splitter from the Focusrite to drive both L/R inputs on the Wiim simultaneously, (3) MAYBE Wiim has a function to mono a single input to L/R, I don't know. I recommend the first option - measure L/R separately.
Re: all the summing questions, I don't know. Those are Wiim questions. Consult your manual or look in your menu.
Re: measuring at higher sample rate. This does not give you higher resolution, this gives you a higher frequency ceiling. For e.g. 48kHz means you can measure up to 24kHz. There is no point going higher than this for acoustic measurements, it is unlikely your microphone can measure that high. Those super-high sample rates are for measuring DAC's and amps.
Re: buffer size. If you don't have any issues with your measurement, don't touch it. You need to increase it if you start getting dropouts or stutter.