After mulling it over, I think I have a plan.
I just bought 9500 RR points ($262) so now I can cover one-way flights that are about $176 each. The flight to Orlando currently has a WGA fare available for $176 and I plan to book that one tonight since I have enough points already in my account to cover it. Also, it is the ONLY option that we have to get to Orlando on that day so I want to make sure I get it. Then, to get home, since the WGA fare is sold out for the flight we want (which lands in GR at 12:05am anyways), I will book the $176 flight that leaves at 4:25pm, stops in Austin, TX, then on to Chicago for a plane change, and then finally on to GRR, landing at 12:05am. It's not ideal, but it is doable, and it is within our budget. My hope is that there will be WGA fares that come out for the flight that we actually want. Then we can change to that one without any issue and we can "lock in" the prices that we are willing to pay.
How does this sound? Is it reasonable, or am I missing something?
EDITED: Ok, I know that paying $262 for the points is more than paying the $176 for one-way, but I have a twisted, incomprehensible reason for doing it that way. It's basically a $90 insurance policy that allows me to book my entire trip with an unconditional cancellation policy. I'm not flying again until 2018 and the points are the only funds I have invested in this trip so far. If something comes up (like my friend backing out), I can get my points back, I can cancel my DVC reservation, and I can use my AP next year.