In the past I would always try to study each individual system.
Such as Tong Long, Bei Shaolin, Wing Chun, Pak Mei, Taiji, Tong Bei, TKD, Judo, Ju-jitsu and the list keeps piling up. I tried this approach for 15 years, then I realized each system had unique approaches to different methods of cultivation. But as for Martial applications I realized what was important wasnt learning as many systems as possible but to learn the four ranges of combat. Tek/Da/Suai/Na- or more loosely stated kicking/striking/throwing/grappling. I'm not saying that I am a big MMA activist or anything for my personal preference I feel that CMA addresses each range as long as you have an experienced Sifu. So thats what my primary focus has been is training each range of fighting as opposed to learning new styles to counter other styles.
But I dont have any regrets about learning quite a few systems I studied each one for a long period of time and gained valuable insights especially in the areas of Fa jing. As well as various Nei Gong training methods.
But given this approach I wasnt ever able to put everthing completely together and make myself better like I thought I could. Thats the number one problem based on my perspective on the style vs style concept. Again this is only my opinion and I'm sure my perspective may change in the future given growth through Wu Gong training.
But I do feel that its necessary to learn and have experience in each range to be a more complete Martial Artist, though there is nothing wrong with only learning one range and perfecting that range if thats the intention.
thats just my .02 cents
take care,