I think partly the difficulty here is the shorter hitting person is much more likely to hit it less far offline. So even if you place tees so the person who hits it 150 hits it to where the "championship" tee players are playing to, the challenge is never going to be the same.
One of my parents' friends, a lady who hits it maybe 160 on her best day also hits it arrow straight. I don't recall ever seeing her miss a fairway. She doesn't hit it far enough to. She would hit fairway then green on the shorter holes and fairway fairway green on the longer holes. She was about an 8 handicap at the time. So to give her a challenging tee shot you'd have to make it very narrow, which makes it a joke from the back tees.
That's leaving aside that it's impossible to have two players of such differing length play to the same spots with both first and second shots on a hole. A 120 shot for someone who hits it 300 in the air is vastly different from a 120 shot for someone who hits it 130 in the air with their driver. They can never have the same questions asked, unless you have the second player playing from 50 yards while the first plays from 120, but then they have very different tee shot situations.
I guess the best you can do is try to ask the same questions of players at different points in the hole. So for example, and I know it's not perfect for various reasons, but the 4th at Bethpage Black, the green approach shot there is very challenging for the top level players with their second shots. They're hitting long irons to a green above them that slopes away. That hole could present the same challenge to someone who hits it 150, but not with their second shot. More likely with their 3rd or 4th shot depending on where the tee goes. Not sure many people who only hit it 150 could make it up the hill to the second fairway, so that hole wouldn't pan out that way, but the green situation could ask the same question of do you play out to the right and leave a decent chip/pitch or do you go for it. If you're comfortable with putting the challenge to a player not necessarily on the same shot, then it doesn't really matter how long the hole is unless you're worried about what your score is.