Is the Valiant 40 a bear to get going? Would a 36' 1977 Cabo Rico ketch, priced at $50K, be a bear to get going?
Or would I be smarter buying a 1993 38' Morgan Catalina MkII at $85K. Would it hold up to my sailing plans?
I think any of the above would be fine boats for your intended plans, if they are in good condition with proper gear. The milk run through the South Pacific is routinely done with Catalina/Beneteau/Hunter types.
As far as speed goes, with those 3: C38>V40>CR36.
If you're mostly planning for Baja cruising and then a romp through the SoPa, maybe considering comfort at anchor should be a priority, since most folks spend most time anchored, not actually sailing.
I personally really like what the V40 offers...somewhat of a hybrid between traditional heavy full-keelers (think W32, Tayana 37, etc.) and more modern designs with a split underbody. While not fast by today's standard, the V40 is thought of as a good performing classic bluewater boat and as you know, has an excellent reputation among cruisers.
Aesthetically, I like the Cabo Rico best, but have seen a few Tiburons badly in need of repair (leaky decks, etc.), which leaves me with questions. I also think you'll have a hard time finding much selection when it comes to CR 36's.