The following post is written in the context that I actually like Herro and think he would fit in well with this team and be a key piece for us going forward. So, if you disagree with that premise, that's okay and you can just throw out all that I'm about to say.
If the Spurs wanted Herro, I think giving up the CHA pick and getting Herro back would be the way to go. This helps POR save face by getting another FRP added to the haul for Dame, when it reality this pick is MAYBE a coin flip to convey and I wouldn't bet on it. POR or MIA could attach a few 2nds coming back to us, and in reality we may not actually be giving up anything.
Is there better value you can get for the CHA pick? Maybe, though I'm not sure. It is by far the least valuable asset in our pick treasure chest, and a pick we probably don't actually want to make (if it conveys in 2024, it will likely be our 3rd - and worst - pick. If it conveys in 2025 it will likely be our 4th (!!!) pick). I'd definitely give it up in order to land Herro, but that is all based upon the first assumption. If the Spurs don't rate him, then its all pointless discussion. Spurs will never be in the business of taking large multi-year contracts for guys they don't want.