At the risk of stating the obvious: It is funny because the game was awkwardly titled: "Sid Meier's Pirates!" and this phrase was all over the place.

Yep - Pirates is "the first game to be called Sid Meier's Something or Other" - almost all of his subsequent games used that title scheme: https://en.wikipedia.org/wiki/Sid_Meier#Games

Im recently intrigued by Solo Flight, although I havent played it yet. The idea of taking that military flight sim base and just turning it into a casual flying-for-fun game is something that resonates with me. I did love Flight Unlimited which is an obvious spiritual successor

This is delightful (from that wikipedia page):

The first appearance of Meier's name on the retail box of a game was as the credited creator of Formula 1 Racing in 1982. In 1984 Stealey began marketing Meier himself, hoping to attract other developers by promoting him as an auteur; by 1986 MicroProse was using Meier's name and face in advertisements for its games. In 1987, the company released Sid Meier's Pirates!, the first game with Meier's name in the title. He later explained that the inclusion of his name was because Pirates! is very different from the company's earlier titles. Stealey decided that Meier's name would make those who purchased the flight simulators more likely to play the game. Stealey recalled: "We were at dinner at a Software Publishers Association meeting, and Robin Williams was there. And he kept us in stitches for two hours. And he turns to me and says 'Bill, you should put Sid's name on a couple of these boxes, and promote him as the star.' And that's how Sid's name got on Pirates, and Civilization."