Were in the same conundrum that happens to a lot of small market teams and thats our "Star" player is entering the end of his contract and he wants to win, if we mulligan the season or go into it with very few upgrades we run the risk of him demanding a trade. I think were going to see a bigger trend of 1 and 2 year contracts for role players with how this new CBA is so if we don't like the market we may be able to give out some 1 year contracts and roll the capspace over while still upgrading the team. I can also see us trading for a player on the last year of a monster contract on a team over the cap looking to shed salary, someone like Pau Gasol, that would allow us to get better while having a large amount of capspace once that contract is off the books.
Is Aldridge really the type to demand a trade though? He's definitely a "star" player, but there's a lot of upside to this franchise, stemming from Lillard's rookie season, as well as all of the young talent on the roster. If the team were in the East this season, they'd easily be a playoff team. With one more season of experience, the #10 pick, and a couple of quality role players added at one (or two) year contract value, like you suggested, the Blazers could very well find themselves in that #6-8 spot next season, looking at a 2014 offseason with cap space. I don't see why Aldridge wouldn't want to be apart of that going forward.
I also think that Aldridge is in a perfect situation for his skillset. If he were really itching to get out of Portland, how many contenders would accommodate his style of play, as well as his salary? He's got a good niche going.
The other aspect I'd been thinking about was similar to this thread, but b/c of maxiep's theory wouldn't necessarily work for us: keeping a large chunk of space (fill with contracts like Pav's--1yr guaranteed) and be the team that lux tax teams run to for tax relief at the deadline (Kurt Thomas for 2 1sts, anyone?). This year's the first of the "incremental" tax, and it counts towards the "repeater" tax rates for next year, so you may be able to see some teams (like MEM this year) desperate to shed contracts. But with half a dozen teams who'll be effectively shut out from the Free Agency game this summer, and have cap space to burn, there'll be competition to be that salary sink.
Additionally, if our GM was a guy like Cho or Presti who was known for being analytic and calculating, this might be an option high on the list. However, I get the vibe that Olshey's more of a guy who'll wine-and-dine the biggest names (which is why I think that, while the chance is still small, there is a chance that Howard and Bynum and Josh Smith actually talk to us--something LeBron won't do in 2014) and that he's much more comfortable wooing a splashy FA than holding on to space and playing the long chess game.
Memphis shed their salary not only to avoid the luxury tax but to also get rid of Rudy Gay. The guy was borderline amnesty material, like ISO-Joe in Atlanta. You're right that our new owner is a cheapass, but the move to bring in Prince instead of Gay was more auxiliary than prudent, like most outlets suggest. It just so happened that this cheapass new owner was faced with an easy decision to cut costs and improve the team at the same time. If you look at the team's performance since Gay, we've been way better off, both in the books and in the way we play.
With that said though, I'm sorta getting mixed messages from Portland fans on the willingness of Paul Allen to spend. On some matters, posters will say, "our owner's one the richest blah blah... fuck the luxury tax." Then on other matters, all of a sudden, the luxury tax seems to be an issue. Which is it?
As far as your hopes for Bynum, Howard, and Smith go, aren't those sort of unrealistic expectations trying to court Bynum or Howard, and as far as Smith goes, why would anyone want to be locked into a MAX contract for Josh Smith?