I seem to remember a CV440 over there. Winair would actually be pretty neat to ride to St. Baarths or Canefield in Dominica. I think there are some Fed Ex feeders that fly from the to nearby places too. The planes are less interesting, but the destinations from SXM are still pretty cool. Is there a C-208 or BN-2 that still runs to Saba?

WinAir is the only operator to Saba in their Twin Otter. No CV440s or any really exotic rides any more. The Fed Ex feeders are 100% Caravans now.
I've got a few hundred landings in each of them, but the more challenging airports are St Barth, Nevis and Saba. None of them are worth jumpseating for a geek day out. I do like the idea though and I might copycat it.

Side question... how do they plan to keep the 727s and CV5800s flying in the age of extended envelope simulator training requirements? Doubt there is a suitable simulator for this.

CV580??? Good question. Possibility of a waiver. B727... Dry leasing a FFS simulator from a Part 142 provider.

As far as I know nobody is updating the software on the 727 sims to meet the extended envelope training requirements. Hence why I asked.

It's not required. If you can fly a 727 you know how to safely fly your airplane when the autopilot kicks off. It's called airmanship. The autopilot on any 727 that I ever flew was only good for climbs, descents and holding headings. Thus we hand flew a lot and learned our airplane.

Where does the reg exempt the 727? It sounds like there is an alternative means of compliance. Just trying to find out what it is.

Nice job patting yourself on the back for flying a 72, though... but I bet there's more than a few of us who've done that.

Apparently you don't have a sarcasm filter for the first part. As far as the second, if you have flown a 727, DC-9, DC-8 or any other first generation transport jet you too probably have decent hand flying skills. That was all that was implied.

Give CAE and PanAm Flt. Training a call. They will provide accurate information regarding your query.