Like I said, I was half-way joking. Sounds like you have more experience than many that successfully pull off the lifestyle. There always seemed to be thresholds that people would reach and wouldn't continue out of fear or funding or just lack of interest. Georgetown, Exuma was always the first one in the Caribbean. The herd would thin drastically making the jump to outer-islands and then T&C, Hispaniola, PR, and the Virgins (and beyond). Getting through the canal also seems to be another stopping point, as things get more serious on the Pacific side.
It does seem like the farther you want to go, the more expenses increase, at least initially. Go outer-island and a wind generator makes sense, plus a SSB and modem (or sat phone nowadays if that's your jam). A primary and backup helm system are a must for open ocean sailing. Go to the Pacific and a water maker is a necessity. Radar is super helpful in Europe. AIS just makes life easier everywhere. And so on...