I think I found an answer to one of my questions - United doesn't appear to have any partners going to Alaska. I thought maybe Air Canada but I don't think they go to Anchorage.

Which kind of gets me back to one main question about whether my destinations are realistic.

I'd be willing to give up on Delta altogether and change my goal to Bar Harber, Maine, which means beefing up my United account (15,000 miles) to 25K. So my question is this: Oklahoma to Portland, Maine would mean at least a couple connections on United. Is Tulsa to Maine doable on a United frequent flyer award in September?

Just looking for your best guess. Thanks a lot!