To answer your first question, it's absolutely worth doing both. Palo has a bit more familiar menu in that it serves northern Italian cuisine with which many people are familiar (pizza, pasta, et. al.); Remy's menu, however, isn't alien, just split into various categories (earth, sea, freshness), but those categories include familiar dishes, as well. Both require an additional charge, but given the quality of food at both, it's worth it for us. Palo is an upscale restaurant with a warm ambiance and more of a comfort food air about it given that the menu isn't quite as adventurous as Remy's. One of the constants on the Palo menu is the chocolate souffle for dessert that is wonderful. Remy is a bit more of a fine dining experience than Palo--think Victoria and Albert's on the sea. In fact, it compares quite favorably with that WDW icon for about half the cost. The meals are served with more of an artistic eye toward presentation and uniqueness than are the Palo offerings; however, the Remy dishes are every bit as savory and delectable. The ambiance at Remy also reflects a bit more upscale view with servers there to help at every turn. Leave to go to the restroom, and they will meet you at your chair upon your return to scoot your chair back under you and replace the napkin on your lap. While the service at Palo is superb, the service at Remy is exemplary.
I suppose it's in the eye of the beholder. I'm certainly not quarreling that the Remy menu is a bit more adventurous, but buffalo, quail, scallops, lobster, Wagyu beef, King crab, veal, turbot, and chorizo--among other items--hardly seem unfamiliar. Having actually eaten at Remy's a few times, we found the selections fairly well balanced between seafood and non-seafood items. One whole section--the sea--certainly is ocean based, but the earth portion isn't, and the fresh menu is usually equally split between two items from the sea and two from the land. The fact the entree titles are written in French is certainly worth noting (though they are largely explained in English) as it could detract from the overall experience for some and make the preparation appear unfamiliar. I wouldn't call the food unidentifiable, however.
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You don't get a full glass for each course - more like a half-glass but there were five courses, plus a cheese course, plus their speciality champagne cocktail to start which was paired with two amuse bouches (tomato soup crouton and something else with foie gras if IIRC). It works out to about three normal glasses plus cocktail plus a small glass of port (which I didn't drink). I might have also had a glass of iced champagne in Meridian before while waiting for our table. That's really hard to say. I had no problems with the amount but some people might find it could be too much. It did seem like the ship was swaying just a bit more than usual on the way back to our stateroom
I suppose you could ask about sharing the pairing, but you'd really want to both be having the same courses or the pairings won't work. DH and I each did a completely different menu so our pairings wouldn't have worked for each other (though we did taste each other's at each course). If you have different menus, you might be better to just ask for a recommendation of one or two glasses of something that would work with one or more of your courses.
As for the last part, the other person can get as many courses as wanted. One of the beauties of dining aboard DCL is they essentially will give you whatever is on the menu at your request. I've done it a few times.
