At some point it sounds like you intend to be OCONUS. That means you will not have many of the back-ups that US boaters lean on - towing services and the USCG to name two. Work up a plan to be self-sufficient including the need to abandon. For me that means three sets of ground tackle, a good RIB dinghy, 10hp outboard, tools, spares, manuals, SSB/satphone, state of the art chartplotter, two handheld GPS and VHF, radar, EPIRB, drogue, storm jib and deep reef main. Solar, hydro-gen, or diesel gen. You should be working on your cruising guide study now. Down island? get a liferaft, and build a ditchbag.