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Most difficult type of hole for YOU

Mine is definitely like this - 300 feet, first 100 is open, then the last 250 is wooded, all while gradually bending left to right, so an anhyzer for a RHBH shot. Btw my flicks suck :p For some reason psychologically, I can play the same hole waaaayyyy better if the whole thing is wooded.
Being that your from Wisconsin, your "most difficult type of hole" sounds very similar to hole #1 at Dretzka.
 
Long anhyzer throws with a hard turn at the end, or short hard hyzers in a tight fairway.
 
Long anhyzer throws with a hard turn at the end, or short hard hyzers in a tight fairway.

Exactly, especially that long anny with a hard right turn at the end.

I will add to that that I have trouble with short hard hyzers where the fairway is long after the turn. I either throw it too far and miss the turn or too easy and so it doesn't have enough to get all the way down the fairway after the turn. What sucks is back in the day when I couldn't thrown more than 250 I'd park holes like this all the time.
 
Wooded S-shots that start out going left off the tee, but end fading right.

My approach is to go with a RHFH flex shot with something OS, but... dialing in the right amount of annie and oomph to hit the initial line, and flex back to the right at the correct point... :\ Let's just say I'm not at all consistent with that. :(

Yeah, any of these longer than like 225' and I'm trouble. I just don't have the FH power for it.

Hole 10 at Rock Ridge in Pittsboro just eats my lunch all the time. It's a wooded tunnel that drifts left awkwardly into a tight, split fairway. I can't hit the landing zone at the bend, always just a little bit short or just a little bit in the trees. Then I end up plinko'ing my way to the basket.
 
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