There are positives and negatives to it. I think most of what we see are negatives, and the fact that some of the players might not cost as much (that's debatable; it only takes one other team to want to sign them for more than the Blazers would) doesn't outweigh the downsides.
The biggest issue, IMO, is if LA was inclined to stay in Portland but has doubts now about whether the team is getting him any closer to a championship. I've said elsewhere that none of us know LA's real motivations or thoughts, regardless of what he might say publicly. So this is just speculation. But keeping Aldridge needs to be Objective A, B and C for this offseason. Maybe Objective Infinity. He is a unique talent, and I don't see the Blazers replacing him if he leaves, and I don't see them being very good anytime soon if he does. I mean we might be talking years out of the playoffs.
The reason the other guys might not cost as much is simply they might not be quite good enough to get the team to the next level. So far, this has been built as LA and Lillard and a bunch of very good role players what make the total greater than the sum of the parts. Now I have concerns that Lillard might be hitting a Stephon Marbury-type wall that will define the player he is for the rest of his career. As for those other guys, I've learned not to fall into your own players ... when I first got to this board I floated an idea of trying to trade Batum and Rolo to the Bulls for Noah, with some parts thrown in (possibly Luol Deng or Jimmy Butler at the time; no longer a realistic option) and got told it was horrible. But Noah gives you a lot of the same defensive qualities of Rolo and is a great passer, which it seems Batum has evolved into to his own detriment (he forgets he is one of five players on the floor he needs to get involved).
Anyway, you have to be open to dealing players you like -- and these guys all are pretty likeable -- to make the team better. Honestly, aside from chemistry, who other than LA really is irreplaceable on this roster? I'd argue none, maybe not even Lillard, having watched his struggles the second half of the season.
Batum is one of the biggest question marks moving forward. He's shown he can be a dynamic offensive player when he looks for his own shot. But he doesn't do it often enough. And the potential of him doing it isn't enough to justify the financial commitment. He has to be a scoring threat. And, if he goes elsewhere, the Blazers need to find a 3 who can defend several positions and is an above-average ballhandler and passer, because our 2 isn't the former and our point isn't the latter. I've looked through rosters, and there aren't a lot of 3s that have that particular skillset. If you don't get those qualities in a 3, then you need to get them somewhere else.
The other big issue is how do you fill the holes. If Aldridge stays, it becomes a lot easier. You have a superstar talent who doesn't appear to have a superstar ego. His presence could attract other good players, because he wants to win and will do anything asked but he doesn't necessarily seem to feel he has to get the attention as the guy that is the reason for his team winning. I think he's more of an exception than the rule, though. A lot of these guys have been told all their lives how great they are. They want to be THE guy and have the spotlight. And Portland, while I've always heard is a great place to live and I know has terrific fans, doesn't put those type of players in a position to get the kind of accolades and endorsements to which they aspire. It doesn't offer the "excitement" of a New York, Chicago or L.A.
That becomes a big challenge for Olshey. You not only have to find players capable of making you better, but you need to find players willing to come to Portland and do it. It can be done. San Antonio has proven that. But is isn't easy. It all starts with convincing LaMarcus Aldridge to stay and then being willing to make some unpopular moves to upgrade the roster.
I honestly feel this team might only be one acquisition away from being a true championship contender (I think the current roster could do it, but it would take an awful lot of good luck, which this organization hasn't had in decades). I'm not sure what that acquisition is, but it's close. You have to hold onto LA, though, or you might as well become Philadelphia West.