here's some youtube playlists (some ive made others i have not) to make it even easier to discover vocaloid music!!
to find info on and keep track of songs, i highly recommend using VocaDB and/or adding the VocaInfo extension to your browser! these tools make exploring vocaloid music much, much easier!!
--velvet

random vocaloid song uploads with accurately translated english subtitles - https://youtube.com/playlist?list=PLAp-i_tkKZNW0zpmnevQbM-T6Nlh0uTO9

greatest hits (2007-present) - https://youtube.com/playlist?list=PLAp-i_tkKZNX5PQ8A9IaVuSnGUMmfPCyC

my favorite non-japanese vocaloid songs - https://youtube.com/playlist?list=PLAp-i_tkKZNVUKmQzmL0g0XyBSK7VKk4V

inabacord (inabakumori station) vocaloid song of the day/vsotd:
season 1 - https://youtube.com/playlist?list=PLkjyFdGsl1_6-E03URXsi7F87YVVmqnhl
season 2 - https://youtube.com/playlist?list=PLkjyFdGsl1_4Y6LAdHnGp6puPhm1VNpN4
season 3 - https://youtube.com/playlist?list=PLkjyFdGsl1_6EGDyX5xK6DAJyFFIXC867

all iyowa songs because iyowa is the best - https://youtube.com/playlist?list=PLAp-i_tkKZNWknSC4E8PqSS-4gsYVKFEU

cool 202x (the latter two also have a bunch of non-vocaloid related stuff on them though)
cool 2024 - https://youtube.com/playlist?list=PLAp-i_tkKZNVDgDV9g-vu5CJyF0QH3x8H
cool 2025 - https://youtube.com/playlist?list=PLAp-i_tkKZNXKbyQX5viGLT2ATv1CYaXr
cool 2026 - https://youtube.com/playlist?list=PLAp-i_tkKZNV9Q-OfJmAGHyUN_A3XbsxW