I am a new-ish (born again) sailor, recently got a Columbia 9.6 (31'6"). I have some ASA credentials, bareboat charter and navigation, although my insurance company didn't even ask me to validate any of those claims (which of course I can) Sateside insurance through Progrressive, is costing me $128 a month, and that gives me up to 200k liability. Which at this day and age is not that much. Most marinas want 300k and up in liability. And I opted for the 1k deductible. This deductible by the way is DOUBLED in the event of ANY "named" storm. I think this has become a pretty standard practice.
This policy and comparable price, is only valid within 100 nm of USA. As far as I know they do not do international.
It stands to reason, that provable experience can help grease the insurance wheels. If you have enough time before your planned retirement, maybe begin documenting every legal "day" at sea, and work toward your OUPV "6-pak" license. This is the track I am currently on, and although I don't know for sure if the "OUPV" license will aid in future international insurability..... I can't think of any way it could hurt to get it. And since I will be sailing anyway.....the extra effort/paperwork seems minimal too me....
Good luck.... Let me know if you find any good international insurance deals for beginners. I have a few mexican riviera trips tentavely planned over the next few years.