We manage our Bonvoy points to $0.01. If we can get at least $0.01 we use points (Ritz Carlton Lake Oconee $499 per night for 5 nights @ 200,000 points) otherwise we pay cash. We were fortunate to get the W Maldives booked in August last year after the SPG merger (April 2019 vacation) for 1,020,000 over the water villa for 15 nights. It's going for 2.5MM points now for a room that cost $1,250 per night.
I would like to here from others where we have the opportunity to get greater than $0.01 per point.
For those managing to the $.01 standard (which I agree is an easy thumbnail starter), are you including the "points lost" in the transaction? For example, in the example quoted above, 5 nights @ $499 would = $2,500 spend X 10 at Ritz for 25,000 MR points + any multiplier for status (e.g., 75% for Titanium would provide another 18,750 points). Use a branded Marriott CC and you get 6x spend, so 15,000 more points "foregone" by using points. As such, I would calculate this as 258,750 points for these 5 nights. You're now below your penny a point threshold.
For me, I start at the penny a point analysis. If it seems like I'm getting a really good deal based on that, I'll use points. If it's just "meh," I usually go with cash.