Have worn both the buds live (my daily) and the buds pro (brother's pair), should have opened the live right at the beginning and worn them, they either fit your ears or don't (only I and my brother in my family can wear them, rest all have too small ears). For me it took a bit of getting used to, and also realize wing doesn't need to be the same on both, have the larger tip in one ear, default in the other, actually caused a bit of pain having it wrong and was on the verge of sending it back. Also check how you're supposed to insert, first horizontal, then twist up so they sit vertical, horizontal they'll cause pain after a while.
Pro has better audio quality and noise cancellation, buds live have all right to good audio (I would hazard that fit is going to be the most important factor for quality), noticeably better if enable noise cancellation, pretty much the same with most noise cancellation, often the mic is used in the earphone to then adjust the audio for ear shape/fit.
If outdoor, would near always pick the live as can turn off noise cancellation while there, and also prefer them for sports since not in ear canal. Have not managed to even shift the buds live while running, weights, jumping jacks, burpees, etc., but this will depend on your ear. Only disappointment, but this is for all bluetooth, is using with VR headset, the latency is just too high, haven't tried the pro, but assume the same, and on desktop as well, but there my over ears are fine with latency outside of competitive shooters (like 50-100ms, but was instantly noticeable on W10 when I wore my galaxy buds live and sis had discord open to the side with 3rd person speaking how I had a good half second delay, sometimes a little more.