I sat next to a NetJets pilot on a recent commercial flight and we chatted about how he usually flies on a day's notice to anywhere within his jet's range (but mostly the Caribbean & Mexico).

I've been thinking about what he said and now wish I had asked him one more question: how he deals with visa issues. A day's notice is not usually sufficient to secure a business visa to most countries. So, how do international pilots do it? Do they just perpetually renew multi-entry business visas to every country they could possibly fly to? I'd imagine this is easier for scheduled service since you can do your schedule & staffing plans well in advance, but juggling border formalities must be a huge headache for chartered & fractional pilots.

Anyone have any insight into this?

Many countries have different, generally more flexible, visa rules for working aircraft crews and maritime ship crews.

mpc1
on an Italian flagged research ship working in Turkish waters

I watched a number of flight crews walk into Panama on Saturday without anyone paying them a second glance. They just walked through the middle aisle of the lines and out the other side. I would guess that many other countries have similar rules for crew in transit.

Most countries allow crew to enter without a visa given the nature of their arrival

One of the few countries that does require crew to have a visa - the USA

I believe Russia is another country that requires visas as well

Many pilots also have multiple passports. I have a friend who flies private charters/bizjets in a small company. She actually has three passports (one citizenship) since one or sometimes two are away for visa applications for a while.

I was thinking that they would have to as they'll be using their passports all the time, no time out to get visas or even to renew.