I used to think this way too. But the breakfast is such a good value at either the StR and the Ritz if you have to pay, it really makes up for it whether or not it is free. As a platinum (downgraded from titanium these days) I greatly value a free breakfast. But. Here is an easy way to justify the value:

Free breakfast at St. Regis - Value $65++ per person

Cost of breakfast at Ritz - $65++ per person
Free daily afternoon Tea at the Ritz - The iced tea/coffee and finger sandwiches, small bites, pastries etc - Easily worth $100 for two (at Maldives prices)
Free refreshments and mini bar replenished daily - Easily $30-$40 a day - Orange Juice, Apple Juice, a few sodas, a bag of chips, etc - Remember a soda is like $10++

I found huge value in being able to open my mini bar whenever I wanted and grab whatever I wanted. Although I paid $17 for a Corona after tax! But sometimes you just want a beer!

So at the end of the day, both properties offer value in their own way. Yes breakfast is nice, but after flying all the way to the Maldives, don't let it be your deciding factor.

Here are my thoughts on the rooms:
Beach Villa at the St. Regis. It's too much of a gamble at this point. There are just sadly too many villas with no beach. It's not even the fact there is no beach, the pool is essentially falling into the water. So you walk out past your pool and you're dipping into water depending on the tide. I was there two years ago in villa 312 and it was an amazing beach villa. Sadly there is no beach there at all right now.

Overwater villa at the Ritz vs. St. Regis. Both have variables that are up to some luck. As a platinum you will have some pull to get a better upgraded room, but it is luck of the draw.

Ritz - Privacy with overwater villas at the Ritz are spectacular due to their circular design. The walk from the OWV to the opposite end of the island would take some time. The resort is quite long and narrow. Maybe end to end it could take 15 minutes? Maybe less. I think it is less of an issue with OWV regarding sunset or sunrise. There is a huge difference for the beach villas depending on which side you are on, and which way the winds are blowing. The main pool is in the middle of the island, so its a little bit of a hike. Not terrible though. Beach cruiser bikes are easy enough to travel around the island. Although an electric scooter would have been better. Management uses those to zip around the island, lazy me would have loved one.

StR - Privacy on the lagoon side is a bit lacking. Pools are cold on the non-sunset side. Although I didn't think it would be a huge issue, the rattle from the walkway did get really tiresome after a while. They were in the middle of replacing a lot of sections, so hopefully over the next few months they fix the majority of it. The walk from the OWV to the main restaurant is quite close as Alba, Whale Bar, and Crust and Craft are all right there. As is the main pool. The rooms are well appointed. The water pressure (at least for my unit) was amazing for the shower. And the room controls all work great. Size wise, the St Regis villas impress with their stature and design. They are just on the cusp of needing a refresh. The deck is splintering and the interior is starting to show some wear. I had a random panel in my closet area falling open.

If it were me, I would pick the dates that work best. Be happy with your "initial" position, and then continue to improve upon it if you can. The St. Regis has a lot of wacky movement with their availability. So I would lock in the Overwater villa, then simply check daily for an improvement. There were many on here that found the 2 bedroom villas go for nearly the same price as the standard overwater villas. I found a great deal on the StR suite and changed my booking from a standard overwater villa. I could've also had the sunset villa for essentially the same amount of points as the St Regis Suite, I chose the space of the suite over the sunset view. I also saw availability for the 2 bedroom as well, but opted against that since I didn't want to be on a separate floor from my kid. Don't count on cash upgrades, because even if they offer them, they are usually way higher than one would want to pay. Particularly during the holiday season. Look for the points availability to open up. They come and go daily though based on what they are trying to achieve from an occupancy and revenue perspective.

I booked the Ritz and paid $850 a night to upgrade to a beach villa, and thought it was completely worth the price of admission. Even though the villa is identical to the overwater villa. I kept hoping they would modify the points required for the beach villa, but they held firm consistently. They didn't play as many games as the St. Regis did with availability and redemption values. Also the cash+points offer on the site, was exactly what was offered by the hotel team direct.

So long story short. The Ritz, if you book the owv, little chance an upgrade will just come your way. The St. Regis, there are a variety of ways you can improve upon your initial position. The Maldives is very much a pay to play sort of place. Book what you will be happy in. If you get an upgrade or improvement from there great, but if not you still got what you wanted. Do NOT book in the hopes an upgrade will come your way. It just takes so much energy, effort, and cost to get to the Maldives (from the US at least) that you really should book what you want, before you even leave.