Suposedly the Vivo XE800 and Tenmak Piano are good around that price range, but I have yet to actually ty any of these value IEMs (still waiting on 6 pairs from Aliexpress). In general there are a few steps you can tke to make them comfortable though, things like comply tips and light weight make a very comfortable IEM. My Trinity deltas are good but become uncomfortable over time due to the weight they put on your ear cannal, so it's definatly something to look out for when choosing. There are also IEMs with ergonomic designs such as the XE800 and Piano which if done well will be a lot more comfortable to wear (but if done poorly will be far worse than the straight design).