I don't see how you think that there is a maximum number of times 2 semi-states could match up. On average there is a 1/3 chance that any SS would match up against a particular other semi-state so if you look at that match up over a long enough time period all that means is that the average should come out to 4.67 times (14*1/3). In any given year there is a chance that FW SS could match up against Merillville SS in every weight class (all 14 of them). It is not very likely, but it is possible. Kind of like there is a chance of flipping a coin 14 times and getting all heads (except worse because this would be a 3-sided coin). I guess I could see your frustration though if it has happened like that 6 years in a row, but I have to believe that it will average out if you stick around long enough.
Each semi-state should see two of the other SS's 5 times, and one 4 times. The past six years, for Fort Wayne it has been 6 times vs. Merrillville and 4 times vs. Evansvill and New Castle. The most times you should see a respective semi-state in the first round should be five times.
The draw isn't so random if the same match-ups occur year after year. Also, if you want to look at it even further, the 189lb bracket at semi-state has been exactly the same the past four years.
Y2,
The odds that any one weight class would be drawn up the same way 4 years in a row is 1/81. There are only 3 different unique ways they can draw each bracket. Considering that there are 14 brackets to draw up every year means that there is a 14/81= 17 % likelihood that this might happen in one weight class. Certainly not that unlikely that you should question the randomness.
I guess that the concept of random draw doesn't make sense to alot of people. It's statistics. Your logic is only the most likely outcome of a random draw. It is not the only outcome. If they were to stop allowing Merrillville semi-state to go against Fort Wayne just because the bracket already came up that way 5 times, the draw would cease to be random. In a true random draw there is a chance that the Fort Wayne Semistate could go against the Merrillville semi-state in all 14 weight classes. There is also a possibility that Fort Wayne semi-state and Merrillville semi-state go against each other in none of the 14 weight classes. Statistics predicts that over time the results of the random draw should average out to the most likely outcome that you feel should happen each year. I hope this explanation helps.