I'll just break this down for you really quickly. If a player is making 19M and that's what he should be making and he's not on your team then he has value to your team, especially if he plays a position of need for your team. So of course you have to send value out to get that player because that player adds value to your team. This isn't rocket science. You're saying that we should be able to send them an overpaid player that they don't need in exchange for a perfectly paid player that we do need and call it an even exchange. Think about this shit before you post it. I'm not saying that a difference of opinion on what the compensation should be for obtaining Anunoby for Bledsoe is unreasonable (you might think the seventh pick is too much) but debating that there should be no additional compensation from us in that exchange is ludicrous. Then you want to question if I know how value works. Zero credibility.
It's really not rocket science. You "breaking it down" demonstrates you are a bit confused so let me try to help.
If a guy is worth $19m and you're paying him $19m, then you are just breaking even. A team filled with that guy isn't going to be making the playoffs, because you should be seeking players that are worth MORE than their contracted amount. This tends to be superstars and guys on their rookie deals.
That doesn't mean that every player that you have on your roster needs to be adding value over his contracted amount--there are loopholes with the soft cap that make it better to have a guy worth something, anything, if there's no opportunity cost (like if you're already over the cap).
The only time you should give up substantial assets to acquire a player is when there's a likelihood of him adding value over his contracted amount (and/or if you have a "use it or lose it" situation with cap space, etc.).
So... looking at Toronto-Portland. If we assume that OG is worth right at his contract level (taking into account his injury history, his potential for improvement, the size and length of his contract, etc.), then Portland should only give up anything to get him if there's no opportunity cost (meaning: getting him won't cut off any opportunities to do something else). Trading Bledsoe's expiring deal would make sense since Portland presumably will cut him rather than guarantee his deal, so it's a "use it or lose it" situation. Giving up a lottery pick is overpaying, especially since there would probably have to be other salary-matching involved to make the deal work and I don't think Portland has bad contracts to dump (and any dumping would make the deal less appealing to Toronto).
From Toronto's perspective: I said that I don't think sending Bledsoe, alone, would be enough for them. They can keep OG with nothing but opportunity cost (trading him for other value) as they can pay him what he's worth and cross their fingers that he improves. The case for accepting Bledsoe is that they could get out from under OG's contract (cutting Bledsoe with minimal cap hit) and use that money elsewhere... I don't know the Raptors' cap situation well enough to know if that would have any appeal or not.
If not? Then the trade shouldn't happen since our agreed-upon at-contract-value OG is not something the Blazers should give up significant assets to acquire.