Gee, the reason the Blazers have shitty assets is because they drafted terribly and also because they lost TWO of their most important players for basically nothing. You can say cap space is worthless sure, but what are the alternatives? Trading away what little assets you have left? Acquiring expensive stop gaps? Either of those sound worse than just letting the guys expire and partially starting over with a clean slate. Most GMs suck when they make moves without a plan, as a result....most GMs suck. However, being a GM on a non-contending or non-attractive destination is really little more than just throwing darts at a wall. When you're making trades, picks, whatever...you're hoping that you get lucky and get a hit (Drafting a Kevin Love, Westbrook, etc. or having Paul fall into your lap).
When you're ALREADY a contender however, that's when decisions get more tricky, and a stupid front office like Orlando or New Orleans fucked up their situation by making terrible moves. Now make no mistake, I don't think the Portland front office should be pardoned because quite frankly, they made some bad moves even when the roster was healthy. Still, right now, at least they seem to have a direction (cap space). What they do with it god knows but at least there's a lot of roads they could take.
/cue posters with sarcastic remarks about our bad front office