An update - I made some improvement. I called Delta and then did say that they couldn't book SkySaver F and SkyChoice Y on the same itinerary, so that appeared to be out. I noticed that there were enough (3) SkySaver F tickets on the 1st segment of the early morning outbound flight I wanted, and also some on a flight that was almost 5hrs after the first one arrived (I initially saw this combo on Northwest's website when looking for awards there).

I expected that I couldn't book it as a regular connecting flight on Delta, but since they do allow one free stopover on award tickets, I was able to book it that way. I'm hoping we can still get on an earlier flight out of SLC, but if not, at least we get in 6hrs earlier than the original flight. These reservations are being held now, I have until next week to confirm and book them. Some questions:

Waitlisting: I'd still like to waitlist for an earlier departing flight out of the connecting city (SLC). Can I have Delta combine the 3 tickets onto 1 itinerary, so I can waitlist all at once? If not, should I still waitlist each one separately, waiting until both potentially clear before confirming the change.

Same Day Confirmed - if the waitlist doesn't clear, I'd pay to not sit around the airport for 5hrs. Since I just want to change the connecting flight, is that the flight that is subject to the '3hrs and prior' rule? If so, I'd be in the air on the first flight, so I'd likely have to line up someone else to call for me to see about changing it for me. I'd prefer to request it before I start flying, but I'm not sure I can do that.

Thanks.

Jeff