Your requirements seem to be less performance, more offshore/cruising, right? In terms of sailing "comfort" you should probably be looking into a performance factors known as "motion comfort", and "capsize ratio" as secondary; this will help describe what the relative ease of comfort and stability the boat will have while sailing. See the following calculators ( http://www.image-ination.com/sailcalc.html
) The light ULDB boats tend to pound when beating to winward in chop and I'm sure you have experienced this on the Olson 30 and J/105. This is much less so in a heavier displacement boat that is not "beamy". In terms of the sec/mile requirement; you will have an easier time finding a boat that is sub-144 sec/mile in a longer LOA hull. I don't think many older/heavier boats under 35 feet LOA will meet this criteria. That number pretty much rules out boats like an older Catalina 30 or Newport 30, etc (A Newport 30 won the PacCup on corrected time in 1998 BTW). The 144 number might be reduced further in 5 years so plan ahead on that also.
I don't think many of the boats you'll consider would be a problem in terms of sailing them TO Hawaii or Cabo (when properly equipped); it's the return trip that will beat the boat and you up. I'll suggest getting on a crew for the HaHa or TransPac/PacCup on a boat that you would consider for your own (including return trips). That way you will get the sailing experience to someday do it single handed and get experience on a boat you might choose or similar. There are also lots of different boats sailing in PHRF on SF Bay and coastal that you can utilize as a "buyer's guide" to help build your short list.
The Dana 24 looks like a heavily built boat on the performance numbers; 8000lbs, 1.7 Capsize Ratio, Motion Comfort 31.5. If you don't plan to race (just do crossings) it might be a good choice for the task. Check out the "optimal blue water cruiser" page of the "sail data" spreadsheet; this might help narrow your search significantly. Looks like my boat (a Newport 41) fits his "optimal" calculation very nicely!