Yes, the layovers to Madison can be horrific- Dallas is frequently an option, and I might once have seen Atlanta.

I feel like the bus connection is a little worse, because you have to find out if the bus stops at the airport or across town, and you have to get your luggage between airplane and bus. (That latter was a bigger problem for me after I got my CPAP, so maybe it would be less annoying for you.)

Best of luck!

Edit: Let me know if you'd like to meet up sometime, or if you'd like to talk Seattle transplant stuff or anything. For instance, cabs are cheaper here, and the flat rate cab companies are pretty good and can be summoned via text message.