We own a Gold week (week 22) at High Sierra. It’s late May/early June, worth 1880 points. I’ve traded into Sept weeks at High Sierra a couple of times but for one reason or the other wound up cancelling. We’ve never actually stayed there (yet- we are staying this year over Memorial Day weekend in our actual owned unit).
My impression is that trading into High Sierra in Sept is not that hard.
Absolutely though buy a 2000 pt or ideally 2200 pt week. You pay MF by unit size, not by points equivalents. So you’re better off buying a unit with the most number of points you can afford. Mid week stays at Hyatt properties are a bargain, if you can use them. For example, I just booked a 2BR Tues-Sat stay at Pinon Pointe in Oct for 800 points. Likewise, you get a Big Bang for your buck in II with Hyatt points (the II is part of your MF)- I just booked a 1BR full week for next Labor Day at Marriott Mountainside for 740 points.
So- if you get a 2200 pt week, and spend 1400 at High Sierra every year, you’d be left with 800 points. Enough for either of those trades I just mentioned.
The only other thing to consider is: if you’d use the unit every year, there is a logic to buying the exact unit and week you want and just using it. It would be pretty cheap to buy.
@bdh used to sell at High Sierra, he could give you an idea of the best units to own there.