It is not too complicated to take different measurements. However, like everything else, there is a learning curve.
The need for taking different measurements is not a requirement of REW, rather, it is done to get measurements at the listener position AND its surrounding area (typically about 1-2 feet around listening position).
The measurements can be taken with the microphone pointing toward the speaker or toward the ceiling. However, pointing toward the ceiling is recommended. The microphone is calibrated both ways (on-axis, and 90 degrees) and the corrective adjustment figures are provided for each.
There are companies that will use your measurements and will develop the filters for you. So all you have to do is get the measurements using whichever software you prefer and email the readings to them. Then they send you the files that you can use with, say, Roon or HQP.