We can cobble together a rotation next year: return from Giles/Stroman, a free agent, Merryweather, Thornton, Borucki, Shoemaker, Pearson by September, Zeuch/Diaz/Perez. There's a wide range of outcomes from a rotation like that, it could end up being great if everything went right. But if it isn't then it's not the end of the world as long as we get at least a few serviceable starters out of it. We can then add elite starters when we are ready to compete again.
Relievers are entirely unpredictable anyway, it's pointless trying to predict what the bullpen will look like in 2 years.
Jansen only needs to be OK with the bat (rather than atrocious) to be a quality starting catcher. He should be given all of this and next season to turn it around.
Of the disappointments, I'd give Tellez and Teoscar more time to see if they can build on their obvious power, Drury can be shot into the sun for all I care, McKinney/Urena/Davis etc are just 40 man depth.
Alford needs to be up to audition for the CF role. Pompey too if he ever comes back.
Grichuk's extension was not a "good" decision but it's not really a bad one either as he's easily movable if he doesn't improve. And if he's just the 2 War outfielder he usually is, then no it wasn't worth locking him up but he's still a net positive.
Overall this is a rebuilding year, wins are basically irrelevant. What would make it a disappointing year is failure for more than a handful of young players to develop, and bad trades returns at the deadline. A good year would be things like Gurriel and Biggio continuing to play well, Jansen and Guerrero to go on hot streaks, a trade haul at the deadline, prospects tearing up the minors.
Right now, I'd give us a C- grade. IMO the biggest thing that's going to effect the end of season grade is what happens at the trade deadline. If we manage to maximise the Stroman and Giles returns, and add to that with trading people like Smoak and Galvis then we could be in a really nice situation.