Here's how I look at it, and why I like the deal:
40% likely Maynor does not justify cap space (whether by play or injury).
No harm, no foul - we lost basically nothing.
30% likely Maynor does well, but it's unsure whether we should re-sign him.
Olshey will survey his options, and Maynor represents an additional option.
30% chance Maynor's injuries are past him and he fully justify the QO.
Olshey has one of the 3 players he said he wanted to get this offseason.
In the last case, Olshey "just" has to make an intelligent draft pick (not easy, maybe move up? maybe buy an additional draft pick?) and sign a FA that moves the needle with the rest of the $ (preferably a Center).
That's my long winded way of saying it's for the future. I don't think Olshey thinks we're making the playoffs this year.
The real question is did the Blazers trade for Eric Maynor with the intentions of making a playoff push or was this more fore the future?