There's very little VHF service
in the Caribbean. Even in the small subsection that most cruisers populate (the E Caribbean chain), you'll find VHF to be of limited value. And while you don't *need* HF capability, the reason it's often appreciated is that reaching the NE corner of the Caribbean (St. Martin) is hard work, made much easier by staying current on wx f'cast info. (It's also made easier by learning
to assess the wx f'cast data yourself and not listen to what Joe, on the next boat over, thinks it means).
HF receivers - e.g. Warren's Yachtboy - are a cost-effective way to have very limited HF capability, altho' one of the many things a SSB transceiver gives you is a much more sensitive receiver (you'll hear far more) and a better antenna
(ditto). Personally, I thought using a Yachtboy was a clever idea until we had one aboard a few years; they are pretty flimsy and, once you start to troubleshoot the fail-prone areas (e.g. the internal antenna
connection), you are introduced to how they can build these highly capable units for relatively affordable prices.
Cost estimates which span a cruising season or a year or two can be hugely misleading for those of us out long-term; this point is made in different ways by several of the previous posts. If you find a boat in the Pacific that's been out for two years, they are still living off the upfront costs of prepping the boat (fresh rig, new systems, initial stash of spares, etc.). If you look at a boat that's been out five years and they are wrapping up their cruising, you'd need to see how well the boat sold before you could evaluate how much money it really 'cost' them to be out cruising and 'using up' the boat. FWIW the annual cost for maintaining a boat that's doing water
sailing">blue water sailing over an extended period seems to average out to 5-10% of the current value of the boat, annually. (See e.g. Beth Leonard's Voyagers Handbook). This may seem quite high but e.g. look at Warren's reference to his future refit
in Oz: two sails and some structural work will probably exceed 10% of the value of his W32 on the American market (~$50K). In addition, a bottom job and perhaps a few other small items will be needed. When we started cruising WHOOSH, our first-year boat maintenance budget was almost zip. We're now starting year 6 and, if I average it out over that period, we're up to approx. 6% on an annual basis. OTOH WHOOSH is in better shape than when we left. This percentage would no doubt be lower for boats that are more lightly cruised, cruised in seasonal climates where the boat sits for 6 months in a winter berth, and/or cruised for a shorter period before being sold or retired to day sailing
Complex subject and tough to extrapolate on, too.