Yea, it's always "the end of the world as we know it" in someone's view.
$35K--that's a big chunk of a change, isn't it? Big part of the cruising kitty to give up without a lot of thought.
The thought that comes to mind is "go with the flow." For me, if I were in your location, that actually wouldn't mean (at this point) going around Cape of Good Hope but rather I'd probably enjoy Australia for a bit and then make a Pacific circuit (loop) eventually ending up in Japan crossing to Alaska then back down to Panama and then deciding if I wanted to go through the canal and fight against the trades for a bit and see the rest of the world...or do something entirely different. If your cruising is "open ended" you have the time and flexibility to change your plans and really live the cruising life. If you have a goal of returning to other things within a certain number of years, then I suppose this weighs more heavily upon you.
I've visited the Philippines for 6 weeks of land travel, snorkeling and diving and that was enough to know that I could spend months there--if not years. A single weekend in Thailand had me wanting months or years there as well. From Thailand, the PI, and Hong Kong you have easy flights to numerous land locked locations worthy of trekking. My $35K would be more likely to go for those airfares. Two years in Japan make me wish to revisit by sailboat. A dream and too many cruising friends who have cruised Alaska (along with reading writings of Hal Roth, the Smeetons, Bob Griffith and others who have done the full Pacific loop) make me think it's a wonderful cruising experience.
So that would have David and my vote--a Pacific loop trip. Of course, I'd try to enjoy the Aussies first! We hope you link up with Kirk soon.
Also, we're sending good vibes towards Lori and her dad. All of the above "loop" talk presumes it following a stable outcome for Lori's family.