As I said upthread, I don't see Portland parting with Simons (especially with Hood out). They reportedly love him and my guess is that any package they offer for Love is centered around either Whiteside or Bazemore and picks.
As for McCollum, per Marc Spears on the Lowe Post last week, Olshey is on record as saying they don't want to deal guys like CJ because Portland has a hard time attracting high end replacements via FA. I understand that some of this is posturing and I have no doubt that the Blazers would move CJ in the right deal. However I suspect that Olshey really believes this to some degree because he has held on to both Lillard and McCollum for a few years now despite a number of pundits saying he had to move one or the other.
Lillard is a franchise icon and if you read Spears' recent piece on him or any other article on his time with the Blazers, its hard to make a case that he will be moved. Things can change of course but the bar for him being traded seems incredibly high, especially given how committed both sides are to him staying in Portland.
Love to Portland just feels like the best fit for everyone at this point. Cleveland gets out from under his contract and either gets a pick or possibly Simons (Altman has to ask) while the Blazers triple down on this squad.
There are two facets to this. First, Cleveland is bad
with Love, so there's no urgency to deal him to get out from under the contract because there's real value to having stable vets in the clubhouse when you're running out a team of prospects (Boston is likely the apex version of this phenomenon). So the idea of Love for Whiteside straight up is likely a non-starter. And the "But next summer they could use the extra cap space to eat more bad deals for low firsts!!!" doesn't carry a lot of weight because they already have around $67 million in expiring deals this year. I'm not saying that someone is going to have to
Knicks up to get him, but they're going to have to give more than another $27 million in expiring salary and a pick in the 20-40 range. (Off topic, but would there be a more hilarious use of their 2021 cap space than to trade for Irving after Durant issues his ultimatum?)
The other facet is Olshey's observations about Portland, which he is likely right about. So a McCollum trade would need to be for more than the remains of Kevin Love. And I can well see why they wouldn't move Simons. Because when they do finally move McCollum, they're going to want to slide Simons into the 2 spot.
If the Blazers offer a pick with limited protections (i.e. top 10 protection) the deal probably gets done. Aside from that, if you're the Cavs, you're better off just holding on to him as a stabilizing clubhouse presence during the rebuilding era, so that you don't end up being the Blatche/Javale Wizards.