Not sure about your plane's range but, St John's, NFL to the Azores was easily doable in a King Air. Would cut quite a bit off the trip if thats a factor. Winds this time of year may make it even faster. Of course, always take the scenic route if it ain't your dime!!
Not sure about the UHF requirements either. Mine was down both times but was able to get PTAPTP reports relayed by Big Guys fairly regularly. But it gets aweful quiet n lonely out there when no one's around! So get ahold of one if you can.
Unfortunately, I cant find my route of flight gouge right now but, check out
www.baseops.net. They have great stopover gouge and maybe even some ROF suggestions.
As for the rest of it, I did my last trip just over a year ago and everything everyone else has said is on the mark as of then!
Have fun, fly casual!
