I strongly disagree that Westone UM2 is better than Shure SE530 in SQ. I heard the UM2s and owned the Shure SE530s and I must say that the Shures were a significant step up from the UM2 to my ears! The UM2s sound dark, muddy and boomy by comparison. Don't get me wrong - they are certainly very good IEMs. It's just that Shure SE530 is on a whole new level of performance IMO. I say that if the Shures are only slightly more expensive than the UM2, they will be a much better choice for SQ. Now, comfort is another thing altogether and UM2s clearly win in that respect. They have better, much lighter cables than SE530 and will definitely be more comfortable for extended use. Still, I would go with SE530 - it's in a different league when it comes to sound quality IMO, and is also quite comfortable for most people to wear.
As for SE530 vs. Triple.fi, I say go with the Shures if you want realistic midrange, well controlled bass, good imaging and excellent overall balance. The Triple.fis' bass is a lot more forward and a tad blurred and sloppy compared to SE530, while it's mids are recessed, less detailed and quite unclear compared to those of SE530. Also, Shure has MUCH better imaging than the Trips IMO - with SE530 each instrument and vocal is clearly separated and occupies it's own well-defined space in the soundstage, while the Triple.fis sound like a sea of music with little to no separation between different instruments and vocals. Thus, overall, I think that Triple.fi only wins in the highs department perhaps, but while it's highs are more prominent and detailed, SE530's slightly rolled-off highs still sound more natural to my ears.
Of course this is all just my own opinion, so take it with a grain of salt. I know many people prefer Triple.fi over SE530, and I can understand why - the Trips do sound more exciting with that forward bass and sparkly treble. It's just that their sound sig sounds unnatural to my ears.