I don't think the iPhone's DAC/amp is the problem (usually they measure good), it could be output impedance, amplification requirements not met, any leakage inside the electronic circuit, there are a million things that can fail. Also, remember to level-match, our brains are used to judge the loudest as the best.
Actually, I found that by looking at the measurements and comparing them to the measurements that my ears like the most I can narrow down my options faster than just listening alone, but that's for headphones/speakers. For DAC and amps, measurements tell you everything you need to know (even of they have the sound you're looking for)