This thread doesn't fit my question exactly, but it's close enough to not open a new thread.
I'm planning a family trip (me, my wife, and 3 children ages 1-5) to Israel at the end of August (15-30). I was originally reading up on all the award possibilities for NYC-TLV, but also made sure to keep an eye on cash prices. After seeing tickets for $750 on google flights (J2 via GYD and DY via ARN), I figured I should check the UR travel portal, as I've got all those sweet sweet CSR bonus points just sitting there. They didn't have the tickets I found on google flights, but they did have something better: JFK-AMM-TLV (RJ obviously) for just $728 - with a discount for the children at $643. So total cash is $3383, and UR points just 225,525. Plus I can use a $300 travel credit on the CSR and save 20k on the points.
I'm not particularly worried about transiting through AMM. The length of the layovers (4:45 on the way there, 2:30 on the way back) is not terrible (lounge with PP might mitigate the issue), but it's probably pushing the boundary for a layover with kids where you can't really leave the airport. Also, timing wise I would have to daven shachris on the plane, and some here have advised against doing so with T&T on RJ.
So the question is this. First of all, can I assume that this opportunity is better/cheaper than any I'll find by booking actual award
tickets? And second of all, is it worth gambling on cash prices (especially with airlines that Chase can book) dropping at some point between now and August - or at least something similar on a more 'acceptable' airline/layover city?