For aircraft i need something I could plausibly buy (less than the average house price in the SF bay area) and yet still has the range to make the longest overwater stretch, which would be from Japan to Alaska, preferably twin engine. I am using a Beech Baron 58P, which is part of the Black Square Baron Steam Gauge Overhaul, I have seen examples for sale listed for 550k USD.
After working out the route its going to be a distance of 33,754 nm with 63 stops in 32 countries, travelling through United States, Mexico, El Salvador, Panama, Colombia, Ecuador, Peru, Brazil, Guyana, Barbados, Sint Maarten, Cuba, United States, Canada, Greenland, Iceland, United Kingdom, France, Austria, Greece, Egypt, Jordan, Bahrain, Oman, India, Thailand, Singapore, Indonesia, Australia, Papua New Guinea, Indonesia, Philippines, Taiwan, Japan, United States.
So far I have made it to Cusco Peru, which is the furthest south I will go as part of the South American leg of the trip. Here are a few pics.

Departing Oakland.

Departing Cabo san Lucas, Mexico

Over Mexico

Near San Salvador

Hopefully you can see my co-pilot

Panama City

Over Columbia somewhere

Approaching Machala Ecuador

On approach, Cusco Peru.
I was a little disappointed that MSFS did not have any scenery for Machu Picchu as its one of the most famous points of interest in South America.
I won't bombard you all with as many stories as when I did the story of the 1924 route, maybe each major milestone. Doing a different AC every leg made each flight more interesting as I got to describe each aircraft and the problems I had when using less capable aircraft. The 58P baron is a pretty capable aircraft and should make each leg less dramatic, which if you were doing it realistically would probably what you would want.