I think the right strategy now is going to be different from the right strategy in a few years. Right now, I would probably advise most good players to either enter the draft or go into the portal every year. It's how you're going to maximize your money.
This should lead to more parity among power conference programs and fewer Cinderella runs from mid majors. This kind of played out this year, with one double digit Sweet 16 team and it was NC State, not a mid major.
Now, the way for a school to be an exception to that guidance for good players to always enter the portal, is to make sure your key players get such a big increase in their NIL bag each year that they don't want to test the portal, while also having a good relationship with them and developing them with a good coaching staff. This probably means overpaying the market rate to prevent them from even testing it - whether that be in guaranteed money or total amount or both. This may annoy your new players, but your reply is just, "We reward loyalty, and if you have a good year and don't test the market next year, you'll be in line to get a big reward like that too." Plus the incoming players will be getting at/above the market value for their services anyway.
All that said, the current dynamic is not good for the sport and it's not the best for the players either. Some sort of collective bargaining and longer commitments or a limit on transfers are needed, more transparency on money earned is beneficial, and IMO they are likely to be the end result because it's in every stakeholder's interest in one way or another. Once that happens, it's going to be more like the old system than the current system. Most guys will transfer zero or one times, and schools will have a little more control over the NIL money whether it's still officially indirect or not.
I would also like to see some sort of cash flowing to programs that lose players in the portal, kind of like the NFL does compensatory picks, so that they can have a fighting chance to build up their funds and keep some of their stars from time to time... But I don't see that happening, because it's not in the interest of the power conferences who have most of the power here.
Looping back to the OP, I'm not sure what the right skillset is for a coach in the current situation is. Have the biggest NIL bags around, be good at the portal, be good at building out contingency plans and executing them when you miss on your main targets, and be good at getting guys to gel and grow as the year goes on. I guess we'll get a good idea of how Red does at that this year.
In the eventual dynamic, I think he's got a pretty good skillset for it, so hopefully the shift towards that happens sooner rather than later.
