After the beta I thought it would be difficult to stay in 1a with only 1 kind of specialists, so I decided to combine a few. I started out with a mix of flat/cobble and hill/cobble racers and was going to decide which would be my main specialty after I saw some talents. Quite quickly it became clear that Yannick would be my main rider so I wrote down a cobble/hill training regime. At the end of the first season I sold 6 riders that didn't fit that schedule and bought some hillers. When my main talent would have been a flat/cobble racer I would have bought 6 sprinters that would fit the schedule.
Of course it was relatively easy to buy some hill talents after their first year, because there were a lot of riders with the same age available after the first season, so that will be more difficult in future generations. For now I'm lucky enough to have one of the better cobble/hill riders, some domestiques for him that can score some points, and also some hillers (bought after season 1) and flatcobblers that manage some results here and there. I even overpayed for some flatclimbers to diversify a bit more
I think when you ride with a specialist team, you need one guy who is really one of the best in their field and apart from that you need a few others who are capable of getting some results in other parts of the season. That's where you have an advantage over the "big" teams that go for the overall classification. They will send their hillers on training camps for the hill classics because there they can get most points, but a specialist team might be able to set up training camps for other parts of the season as well depending on the calendar and in that way are able to achieve some good results with riders that would not be able to compete for top 10 when all other specialists are there.
Just some of my thoughts on this subject...