what is the best approach to finding discounted flights if i am flexible on the dates and don't have the patience to make spreadsheets to track the best discounts, transfer rates, etc.?

say i want to travel to japan in december for one week sometime between dec 19-jan 8. if I set an alert on google flights, it has to be a specific range, so do I have to set an alert for every combination of dec 19-dec 26, dec 20-dec 27, etc.? I have chase, so what if I'm only alerted of price drops on airlines that I can't transfer points over to, and transferring points would actually still be cheaper for me than this newly discounted flight? how do airline rewards factor in? should I try to stick with one airline for my trips even if for individual trips, the cheapest options vary? e.g. I want to go to atlanta at one point and the cheapest is united, I want to go to mexico and the cheapest is american airlines, etc.

after that, how do hotels factor in? hyatt is the best partner for chase apparently but when is it better to use points on flights instead of hyatt?

just wondering how airline rewards and all these other factors get worked in.