Another tip, particularly if you are a Platinum or Diamond and have the ability to redeposit points (so there's no risk): If you see a flight that meets your available points but has a crazy routing - it's worthwhile to book it and bide your time. If the points then drop at a later date on the routing you want, you can call Delta and they will make the swap for you. But more importantly, booking this far out there is inevitably going to be a schedule change. Delta's policy is that if your flight departure or arrival changes by more than an hour, you are entitled to change to another flight for the points already spent. I think this applies to any segment but I am not certain. While the policy is officially an hour, unofficially it seems to depend on the Medallion desk agent who takes your call.

I just did this for a TLV - CMH flight next January, which I booked on the first day it came available. My original routing, at 70,000 points, was TLV - JFK - DTW - CMH, departing TLV at 12:10 AM and including a 10 hour layover in DTW (ugh - but all the others were 100k times 4 tickets and I didn't have enough points for those). The TLV departure changed last week to 11:30 PM (40 minutes earlier) and with that change, the Medallion desk agreed to change my routing to the one I actually wanted, TLV - JFK - CMH with no DTW layover and getting me home six hours earlier. Schedule changes can be your friend!