First off, let me state that, if the Blazers wanted to avoid these tiebreaker scenarios, perhaps they should have won just one more game over the course of the season. I'll also make the assumption that all divisions are roughly equal and that wins are the true measure of what team is best over the regular season.
Why is "divison winner" the first tiebreaker for playoff seeding? San Antonio is the #3 and Portland is the #4 because San Antonio won their division, and therefore get a tiebreaker. Except that, the only reason that San Antonio wins the division is because their divisonal rival, the Rockets, are one game worse than our divisional rival, the Nuggets. That is, San Antonio is winning the tiebreaker because they have a worse team in their division than does Portland.
Think about this - it makes no sense. Portland hade a theoretically tougher schedule - playing additional games against Denver rather than Houston, still manages to post an equal record, and gets penalized by the rules.
A more sensical process would be, say, record against ther 3rd division in the conference, head-to-head, etc. But divison winner is so dependant on strength of divison that it's really unfair to use as the first tiebreaker.