Ben, there are 10 obstacles that can exist and are rated on every hole. These are:
1) Topography - Elevation change on the shot to the green, and an evaluation of the difficulty of the stance from the various landing zones that the player is supposed to play from. Primary modification is if the green surface can not be seen from where the shot to the green is played.
2) Fairway - Primarily the width of the fairway vs the length of the hole. Modified by things like the player laying up or a tilt of the fairway that would make it play narrower.
3) Green Target - The size of the green relative to the length of shot being hit to it. Modified by things like visibility and if the green slopes to the back.
4) Recoverability and Rough - The length of the rough, the type of grass and the green target value are the primary factors. Things like mounds, hollows or hills modify it.
5) Bunkers - The green target and the percentage of the green surrounded by bunkers give the basic number. The depth and whether there are fairway bunkers are the primary modifiers.
6) Out of bounds - The distance from the landing zone and the length of the shot determine the value.
7) Water - The distance from the landing zone or the length of the carry and the length of the shot determine the value.
Trees - The nearness to landing zones and the difficulty of recovery are determined.
9) Green Surface - Speed and slope.
10) Psychological - A value that is determined by the number of high numbers given on the first 9. Also the first and last holes get some points.
Each of these gets a value between 0 and 10 (some such as Green Surface and Target always have a value above 0).
Each is evaluated for both the scratch and bogey golfers based on their shot distances and landing zones.
Once all the holes are evaluated, the numbers for one obstacle get added, multiplied by a weighting factor (different factors for scratch and bogey) and added together to come up with the Obstacle Value which is added to the base length value and the rating is determined.