I thought about this a lot but I didn't go down the SSB transceiver route because of the initial setup outlay although admittedly once you've got it there's no further expenditure. Instead I bought an Iridium phone, a good antenna and signed up with Mailasail for airtime and email access and so far its all performed very well.
We left the UK two years ago and sailed to the Canaries, Cap Verde Islands, Brazil and then north through the Caribbean, Bahamas and we are now in Florida still north bound.
I use the Iridium to download GRIB files daily and when we got to the Bahamas we signed up for Chris Parker's excellent daily email weather service. Some Americans we have spoken to used both Chris Parker's SSB forecast and also backed it up with his daily email because they said it was sometimes difficult to write as quickly as Chris spoke!
The nets throughout the Caribbean and Bahamas were on the VHF so we didn't miss out much on the daily news and contact.
In the US the Coastguard constantly broadcast a good local weather forecast on VHF but our European ICOM set wouldn't receive it so we invested in a cheap US handheld set so we could.
The Iridium phone (the Extreme model as it has the DSC type service with built in gps ) and antenna cost me around £1400 and when we are on the move I use about 50 minutes of airtime a month.
.......but I am thinking now of buying a low cost SSB receiver just so I can pickup Navtext as we move north!
+1 (with exception of considering an SSB) Iridium every time, for reasons stated, now available for less than the £1400.00, + in an emergency, instant access, and anywhere in the world, they have the best coverage.