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MSC now states web check-in officially begins 30 days before sailing, but in actuality you can usually get most of it completed way before that. Boarding documents are something different and usually become available 20 days before sailing. Of course there are often variations to this timeline.

You were given bad information. While you won't need a new cruise card, on US sailings you will have to get off the ship so it can be zeroed out for immigration purposes. On many MSC US cruises lots of people get delayed boarding while the crew searches for people who don't understand this is a necessity for US sailings.

Likely not covered by the MSC drinks packages....

I've seen posts here from email conversations with MSC/Plusgrade stating items pre-purchased, like beverage and internet packages, are factored into the Yacht Club bid acceptance algorithm. So theoretically if you book an inclusive rate or buy them separately it would give you an advantage versus the same bid by someone without them. In practice I don't believe this is 100% correct and shrewd booking/bidding can prevail. You can cancel the package anytime before the bid is accepted (within two days of sailing) but not after a bid is won. If you don't get the bid accepted early enough you won't have time to pre-purchase and will pay the on board 15% gratuity on the drinks package. Four days is likely a correct guess since MSC seems to make the bid acceptances well before that.

The ship's Technical Sheets list the number of YC cabins. https://www.mscbook.com/shop/TAPortalExternalView?catalogId=10001&langId=-1004&storeId=10757&taportalIframeKey=MENU_TECHNICAL_SHEETS&marketCode=USA

Here's a link to the MSC US booking website showing drink package prices, you can link to your booking country website if it's different. Yacht Club comes with the Premium Extra package. After looking at the bar menu prices you may find the Easy Plus package acceptable. MSC usually offers an inclusive booking rate where the packages are less expensive than outright purchase. If the inclusive rate includes a lower package you can upgrade to the higher package for the price difference https://www.mscbook.com/shop/TAPortalExternalView?storeId=10757&catalogId=10001&langId=-1004&taportalIframeKey=MENU_BEVERAGES&hideSideBar=true

There's YC cabins available for the 14 day cruises from Martinique, very limited numbers. Now I can't find any 14 day round trip from Pointe-a-Pitre, just the 7 days. I don't see any ( 7 nor 14 day) itineraries with embarkation in Barbados on the Italian, German or French websites.

You can watch YouTube Europa videos of both cabins and see they both have walk in showers and a separate jetted bathtub.

Sorry, mistyped on Pointe-a-Pitre in above post. Yes, I see those 14 day itineraries are missing from the US website. They're still available on European MSC sites. I've no idea if they are just temporarily gone or if MSC no longer plans on offering those 14 day itineraries to North America. I agree about the flight logistics from the US. Barbados is usually most practical but MSC has always severely limited inventory from that embarkation port.

You can book the 14 day versions from both Martinique and Port a Prince. The sailings from Barbados are very limited regarding YC and even some limits on Aurea availability. The possibility of upgrading to YC on a Barbados sailing will be next to nil since those cabins will be offered to people sailing from the other two ports.

You're not likely to find live Sinfonia reviews in this area, but plenty are in the CC reviews section. https://www.cruisecritic.com/cruise/msc/msc-sinfonia/reviews

The MSC online purchase area has several quirks as you described. The couple's spa pass is for two people, you only need to select one package for the two of you. The only reason I can figure for offering it to either of the listed passengers is so you could direct any associated Voyagers Club points to a specific person. The pre-purchase area will let you book many unnecessary items like beverage and internet packages even though you might already have them included with your booking rate.

@JamieLogical I just noticed the May 4 sailing did drop another $100 per person on the Drinks & WiFi rate. Not a Flash Sale but very attractive price.

It's normal to still see your original experience online and on the booking confirmation document, but the cabin number will be updated. On your actual cruise ticket you will see a section stating the upgrade and what amenities it includes.

Other cruise lines do have Covid policies, usually that if you test positive as many as 14 days before sailing they will deny boarding with absolutely no FCC or re-booking. Basically they are policies to discourage people from reporting illness.