No, not strange, per se. Just inconvenient. An unnecessary extension of what is already - by definition - an 'interruption' of one's vacation/holiday.

Most upscale/luxury resorts add a 'tip' or 'additional tip' line to final bill on checkout. Maybe CJ does not, but if not, they definitely should. Infinitely more convenient and less stressful than figuring out a % tip and signing your name several times per day.
Most resorts also nowadays split gratuities between all service employees. If not, that would be the only reason to have individual tip lines on each check.

In short, I love tipping, but I really dislike the 'signing for everything' policy that seems to still be in place at several hi-end resorts. Once, at the end, should be enough.

Actually, it is the only safe way. I also appreciate it sometimes when the prices are not so clearly defined to see what the fun then cost. If I am offered water, for example, it is exciting to see to what extent it is charged. In my view, it is a matter of course that has gone out of fashion to hand over the receipts to the guest at the end.

I'd like to know where they sourced that fine, plastic/carbon-molded white fence.
It's magnificent, and its placement gives this side of the pool a more open, less constricted/caged feel.

Hmmmm.
I wasnt thinking about shuffling through a big pile of receipts at the end. But a clearly marked inventory about what u spent. I find this much easier and far more convenient.
I also think the signing-for-every-last-thing-every-moment thing seems to be - at least where i've stayed over the past decade - to be a declining trend.
Happily so, for me.
I understand one doesn't want to find out later that a glass of water costs $20, but one can just as easily question/complain - and to a more-empowered employee than waiter or beach attendant - at stay's end.
(Ironically, signing all the time doesn't make much sense from hotelier/ownership POV either - do you really want to be reminding your guests how obscenely expensive every last item at your hotel is on an hourly basis?)

But man, thank you so much for this 'trip report'. I had no idea such a thing/sub existed, and when the content is from a trusted FTer like yourself, just incredibly fun to read.
I'm not planning a trip anytime soon, but unlike soooo many other locales discussed on FT, I know me the high-end Caribbean market.
I've been to every (inhabited) island, most multiple times.
There was a point (maybe as recently as ten years ago?) where I could have truthfully said "I've been to them all" (meaning the luxury hotels).
That's changed as, just like so many luxury markets worldwide, the number of openings/re-brandings have exploded.
So there's now quite a few (particularly in St Barts, T&C, Bahamas) I have not tried (yet!).
But it's especially fun to read other discerning/tasteful folks' takes on destinations/resorts one knows well.
THANK YOU for this report, I had a blast with it.

One big difference between us is that i am not that much of a foodie.
I can appreciate a michelin starred restaurant (ive found I usually prefer one star to two or three, though - less pageantry, less chance of a 5-hour meal). I just don't claim to have as discerning a palate as most seasoned luxury travelers seem to.
I think it's a great plus for a luxury property to have a fantastic eatery onsite. But if the location is great, and there are excellent restaurants close-by, it's not a big deal for me.
You seem to be closer to the FT norm - indeed, the 'luxury traveler' norm - in that excellence of food quality (and presentation, location, service etc) is a hugely important factor in your overall assessment of any trip/hotel.

Have stayed at three of your four places - StR in MIami being the one I haven't - two of them twice (CJ and FSSS).

Two was enough for FSSS. First time on my own dime, second on client. Just always been hard for me to get behind FS as a brand, or at least for me to naturally lean towards any FS location if something similar is available close by. I've tried a bunch. A few have been exceptional. A few have been dismal (at least at pricepoint). But in my experience, some majority have seem overpriced for what you end up getting. Most are beautiful, or at least 'handsome' looking', but the design never excites. It always seems to net out 'safe', somehow, 'beige'. Uninteresting.
This particular Surf SIde installment is a fine hotel, no question. But it's exhorbitantly overpriced (like everything else in Miami right now), and the interiors haven't felt very 'of place' to me. Dark-ish, moorish, just odd for Miami. Their pools are easily bested, in just about every respect, by those at at least 4 or 5 other hotels in town.
In general, i find it to be one of the nicer Four Seasons I've lodged at, but there's several other Miami/BalH I'd choose well before it.

StR looks nicer to my eyes - at least in certain respects - may give it a go.
I'm kind of a Setai loyalist tho. Well over 10 stays there (mostly for work, short trips) and it's not perfect, but it seems to me the most consistently fine.

Sammana, once was enough. About 12-15 years ago, w wife. (Sorry, we've done so many carib trips that they now kind of blend into 'general' timeframes). Like you, combined with a CJ stay. I believe this was before Orient Express rebranded, and possibly before OE even acquired the hotel, can't remember.
We were extremely underwhelmed, particularly at price and especially compared to CJ. The rooms and decor looks just as dated and in need of a refurb as your pics do. The room felt furnished like your sweet grandma's nice condo in Clearwater, Fl. Fake plastic rattans, wickers, canes, ugly (and worn) upholstery. Cheap blinds. Honestly, it felt like a wyndham room to us back then, and kinda shocked to see the similar setup now.
Yes, the beach is pretty nice, if crowded. We spent most of our time here gazing longlingly back at CJ on Anguilla.

Cap Juluca a completely different animal, both then and now. Have stayed there four times. With this perspective, I have to congratulate CJ for simply still existing at whatever (high) level of luxury it still does.
First three trips were when the hotel was privately owned (usually a big plus over any kind of luxury management chain, i've found, and i mean any kind of chain you can name) and i forget the family's name, but they did a notable job of building, running and keeping this dreamy place up. By the third time we stayed there, yes, we could see why they were looking to sell at that point. By then the place clearly needed capital for upgrades, repairs, etc.
20 years into its history, it had fallen a bit, but not much - still splendid.
Then, most recently, just pre-covid, we were really really pleased to see what a great job Belmond had done.
I never understood the moorish/spanish architecture in this locale either, but i've always loved it just the same. It works somehow.
Rooms/suites/villas and their bathrooms in particular were, for a good long while there, the best hard product in the Caribbean. They wisely kept the same general footprint/layout, but w some truly meaningful refreshes/refurnishings. These rooms were long ago out-gizmo'd and out-splendor'd by other carib hotels, but i still think the rooms are great.
Ditto the new pool, i mean, just a transformative change/improvement. CJ went from having one of the worst pools (at pricepoint) in the caribbean, to having - if not the best - a fairly spectacular one.
Again, not Mister Foodie here, and i do actively shy-away from branded hotel restaurants that try to claim some association with names like "Cipriani" or "Maxim's" or even "Nobu". (I'm even slightly wary of the 'originals' of such things, by this point).
Ergo, we didn't hit that Cipriani place, but we found all the food at Pim's really quite good (and the setting is singular).
Was the food at CJ the absolute highlight of the trip? No, i barely remember it. But we enjoyed it, and the other (third) restaurant.

One other note on food, in general:
Caribbean not exactly known as a hotbed destination for haute cuisine. Or even 'really good food'.
If anything, i think 'fine dining' is known to be among the Caribbean's few 'weak links'.
It's just not among the top 5 (or even 10) reasons people go there.
I always try to stick with relatively simple fish or chicken or produce-based dishes, and the times i've found hotel food to be purely awful have been few/far between.
(Miami a different story, of course, i'm talking here about the islands).

Thanks so much for providing all of this fun reading and viewing!

Thanks for your thoughts. I'd be interested to hear how you like the StR.
Personally, I'm a big fan of FS. I've never had a really bad stay, but have also avoided the less recommended houses.
When it comes to food, it doesn't always have to be Michelin star. I'm also happy with a good, simpler meal. It just has to fit the overall concept. For example, I love to just eat a GOOD pizza in Italy. But quality is an absolute must. This is especially true when high prices are charged.
It is interesting in this respect that Anguilla is positioning itself as a foodie destination.
The resort you are referring to is probably the Aurora. I had read about it in advance and actually wanted to try it out one evening. But then I did not do it.

I am glad you didn't try, I am afraid the result would have been similar to your other attempts.

Actually, St.Martin has been positioning itself as THE food destination in the Caribbean as long as I can remember. And as long as I have been going there, more than half a dozen times in the last 30 years, they have never failed to disappoint. There was always this or that French chef who had arrived to revolutionize Caribbean cuisine, and failed, and went back to duck breast and leg of lamb. In my book French cuisine does not translate well to 90 degrees and 95% humidity. Yet they keep trying, and continue to market to people who actually believe that some veggies and a dip arranged in an artistic fashion qualifies as a "first course" in a high end restaurant. For me and my food porn circle it does not, so we will continue to go to the Lolos in Grand Case where you get a decent meal for a fraction of what you would pay at one of the "high end" restaurants.