My 2 cents:
Avenger II: Not the main icon of Breitling but nevertheless very recognizable a Breitling and one of the more popular models. The most rugged model in the Breitling line. Suitable if you prefer a rugged and masculine looking watch. The most obvious downside of this model is the lack of in-house movement. It's like buying a Bentley car with a Toyota modified engine. Highy reliable and proven, but lacks the exclusivity.
Chronomat 44: The flagship model of Breitling, descendant of its ancestor that revived the Breitling name back to its success. The first head to toe in-house Breitling watch, which no other models can ever replace its title. IMO it contains all the essence of Breitling. Aviator and diver watch, formal and also sporty casual look. Croco strap, calf leather strap, pilot bracelet, mesh bracelet, rubber strap, ocean racer strap, etc...any straps, any color, it will fit asethetically. This is the only model that pretty much covers everything, which so far I don't see a second watch that commands such versatility. If I have to mention a downside, it will be its polarizing design(bezel and centre square) that many dislike. It's not a downside if u don't care what people think of yr watch. But if you prefer a safer design, you can go for Chronomat Airborne instead. However it's just classic looking, that's all, nothing much to talk about. Also IMHO, the rider tab bezel makes the watch looks more solemn and technical, like Navitimer, which doesn't really match that well with sporty outfits(I personally tried it). The bezel numerals on the Chronomat 44 makes it look more sporty and recognizable without losing its refine and elegance, because of its sleek case and sharp looking dial. I have worn it on formal, smart casual, casual, and even sports attire for gym. It matches anything. This watch also doesn't bore me because it contains many details that not many can perceive and understand. I would often stare at my Chronomat for a long time to admire and analyze the design and details, why the centre square is designed in such a manner, why the hour markers are cut to complement the square, why the bezel fonts, how they lower the bezel to facilitate gripping, how the appearance changes as light plays over it, etc. It's like an abstract painting that either you appreciate and understand or you don't. I seldom do that with my Navitimer and Batman because there isn't much details for me to analyze. Everything is just classic and anyone will just say, "nice", and move on. Well not withstanding that I do take out my Navi sometimes so as to practice using the slide rule.
Overall I personally recommend Chronomat 44 for its history and achievement, which will become a legendary classic many years later. It has the in-house exclusivity, design wise it has the versatility. Character wise it is very recognizable and iconic looking that doesn't look like a one percentile watch. Timeless wise I don't think it looks dated that many feels it does, because the design is not over the top, but only several details to add character to the watch. However as indeed several design elements are not something that the past will have, for that I guess it will just have to withstand the test of time.
Good luck with yr choice
