Pitt absolutely SHOULD trade Reynolds now for a package multiple top 100 prospects, with at least one of those being a top 25 prospect. The problem with that is, most of the the teams with best farms are not competitive this year. Tampa, San Deigo, and Toronto are the only clubs in the top 10 farm systems who are competitive.
Among those, Tampa is the only team with an obvious need for Reynolds. Would Pitt deal with them again after they got burned so bad on the Archer trade? If they were ran better, the obvious answer is that you don't let past transactions influence your current situation, and you take the best package available to you. But being that they are poorly run organization, I'm going to guess that they will avoid big trades with Tampa for the near future. Maybe Cleveland would also be a fit. They have some interesting prospects and big need for offensive fire power.
Either way, if they played it right, Pitt could set themselves up for a nice little window in 3-4 years if they sold high on guys now. Could easily have the top farm in baseball by trading Reynolds, Frazier, Moran, and Rodriguez this year. Honestly, the only guys they shouldn't consider moving are Hayes and Brubaker.