Masayoshi worked as both a painter and woodblock printmaker. He studied first under Shigemasa Kitao, followed by Eisen’in Kano in the 1790s. Masayoshi’s printed works, ranging from single sheet prints to illustrated books, were produced under the go, or artist name, Masayoshi. He assumed the name Keisei Kuwagata in 1797 when he was appointed the official painter of the regional lord of Tsuyama. During this period, Masayoshi worked mainly in a Kano style, though he completed some printed albums as well. He also produced ryakuga-shiki manuals, which taught aspiring artists to paint in a quote, "abbreviated style".