I am not an expert at this but have been doing HS scorekeeping for the past two years. I always go to the ordinary effort definition. (below) Hitting the glove is meaningless IMO. If an outfielder gets a great jump and makes a dive and the ball hits his glove...so what, a great play almost made, but it is a base hit. FWIW I do tend to have more questions on plays in the outfield. IE if an outfielder gets a bad jump on a ball and it falls in for a hit then it is a hit. (I hate this being a pitchers dad..) Now if he is tracking it and then misjudges it and it falls around him - glove or no glove I will give it an error. The other problem area I have is with flairs and you may have three fielders converging on a ball. If they all pull up at the last minute and if falls in then generally it is a trouble ball and I give it a hit. There are times when they are standing around and it is a clear E, but I have trouble in who to assign it to, generally I give it to the outfielder since he should have been in control of the play.
I always discuss questionable calls with others and we come to a joint decision. If the play involves your kid then you are automatically excused. This gives our books some credibility. If there is a really questionable call I will ask the coach after the game.
That said this is not little league and I have actually never seen an inside the park HR in HS. I have seen aggressive outfielders dive for balls and make a single a triple however.
I drifted all over with this reply, but if you really want to get an answer ask the coach and take the decision out of your hands.
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ORDINARY EFFORT is the effort that a fielder of average skill at a position in that league or classification of leagues should exhibit on a play, with due consideration given to the condition of the field and weather conditions.
Rule 2.00 (Ordinary Effort) Comment: This standard, called for several times in the Official Scoring Rules (e.g., Rules 10.05(a)(3), 10.05(a)(4), 10.05(a)(6), 10.05(b)(3) (Base Hits); 10.08(b) (Sacrifices); 10.12(a)(1) Comment, 10.12(d)(2) (Errors); and 10.13(a), 10.13(b) (Wild Pitches and Passed Balls)) and in the Official Baseball Rules (e.g., Rule 2.00 (Infield Fly)), is an objective standard in regard to any particular fielder. In other words, even if a fielder makes his best effort, if that effort falls short of what an average fielder at that position in that league would have made in a situation, the official scorer should charge that fielder with an error.