Oslin's musical success allowed her to become more financially stable. By 1988, she purchased her first house, but was rarely home due to a demanding tour schedule. That year, she toured with Alabama and George Strait, and recorded her second album for RCA. In August 1988, "This Woman" was released. Oslin wrote (or co-wrote) all ten of the album's tracks. According to Oslin, "This Woman" reflected the modern thinking of middle-aged women of the eighties. The project received critical acclaim from various publications. Alex Henderson of Allmusic gave it a three-star rating, calling it "a generally appealing release that successfully balances commercial and artistic considerations." "Rolling Stone" named it one of their "12 Classic Albums" in 2018 and found it to define female independence. Rock critic Robert Christgau gave the album a "B" rating, praising the album's defiance of gender roles in the Nashville establishment. It produced the number one hit, "Hold Me," which would also win her a second Grammy award. It was followed by the top five hits, "Hey Bobby" and its title track.