I guess it's more of a context that's getting you perplexed. 二浪　＝　二年浪人 "浪人（ろうにん）" is a person who could not pass an entrance exam to a school (usually university), and is still studying to get into the school. "浪人" status will be lifted once they are accepted to a university. Sine entrance exam is conducted only once a year in Japan (as far as I know at this point), "浪人" is a status given for a year. If you are not accepted to any university (or decide no to go to any) after a year of "浪人" status, then it means you repeat the same status twice, meaning "二年浪人". Japanese love to shorten words, so we shorten the "二年浪人" to "二浪". There are also "三浪", "四浪" ...etc. This "浪人" phenomenon generally happens as many Japanese hold the beliefs that so-called "elite university" will guarantee their career, as well as a higher socio-economic status. Now this is up to "二浪". Next, "二浪中の身で" needs to be broken into two parts: "二浪中" which means "in the middle of the status of 二浪", and the other "の身で" which is an expression to describe your status, usually with a connotation of degradation compared to others. So this will be translated into "under/in the status of '二浪'". "てしまい" is a run-off of a sentence. The sentence is supposed to continue after this clause if it's formal writing, but in casual style, we sometimes write or say this way to emphasize the event that happened up to the point, and to make listeners or readers anticipate what story comes next. So here, we don't know what happened after s/he dropped off the prep school after two years of failing to proceed to university/high school etc. I hope this will help.

HI Jordan, I think I can help you with this. I would break the sentence into the following bits: とうの昔 (a very long time ago) 二浪中 (in the second year after failing a college entrance exam) のみで (only ) 予備校を (prep school + object marker) 辞めて (quit) しまい (verb ending denoting an adverse outcome) In other words, "のみで” is not "の身で”, and it means "only." The entire sentence means: A very long time ago, only those in the second year after failing the college entrance examination would quit preparatory school (where one studies to take the college entrance exam again). I guess the above sentence implies that in the past, people didn't quit in the first year in preparatory school. Note on shimau: Shimau alone means "to finish" or "put away (something)," and it retains the same general meaning when combined with a verb in the Te Form, pointing towards the completion of a task. Since shimau is a standard verb, you can also conjugate it in a dozen different ways. A few examples are: Shukudai o shite shimaimashou. (Let's finish up our homework.) One other role that this Te Form + shimau plays is to express the doing of something which was hard to decide to do, doing something unexpected, or the happening of something unexpected: Kuruma o katte shimaimashita. (I bought a car.) And that's not all. Shimau is also used for expressing concern about the possibility of something negative happening and/or the dismay at finding out that something negative happened: Watashi no fuku ga yogorete shimau! (My clothes'll get dirty!)