The only time I look at it is after I have chosen my destination, but not my dates. from there I review the cost of the flight, if I'm willing to pay that OOP, or if I want to use miles, then check availability for dates (assuming I have a selection of dates I CAN go).

Long ago I stopped looking for optimal usage and started focusing on I just want to be there and enjoy as much as I can". so Europe, its almost always OOP because by the time I can plan it, the free ones are gone. For anything south (carib, south America) or most domestic, its miles because just sitting in my account instantly devalues them, so they need to be spent as I earn them.

I cant remember the last time I sat with more than 200k miles at any one time, the programs screw up the rules to quickly to rely on them being a value anyway.