After reading over your comment a couple of times, I believe that I've got the gist of what you asked. You want to index the appropriate text references to 1) the right category and 2) the right person/page number(s) for that category. If I've got this right, this is going to be a lot easier than you think.
And you're well on the way to getting it done efficiently, if not quickly with one of the workflows you've figured out. From there, all it will take to do things right is attention to detail. Since Harry seems to be a winner/offender in all the categories you used for examples above, let's use his name in vain to illustrate how this can work for you:
Most important – Before you create any index entry, review and understand what index entry(ies) you want to make. Because if you want to make multiple entries for the same name, you can (relatively) easily:
1. Let's use his Art Direction award on page 12 for our example. Highlight Harry's full name in the text. If you haven't already learned the keyboard shortcut Cmd/Ctrl+7 (for Macs or Windows systems, respectively), use it now and remember it later. You'll come back to it ... repeatedly.
2. Using the keyboard shortcut opens the Index Entry dialog box, which you can also do more slowly by going to the Index panel's flyaway menu and selecting the New... command.
2A. The Topic Level 1 edit box should be highlighted with Harry Weber. Click the downward-pointing arrow between the two columns of edit boxes to skip Harry's name to the Level 2 edit box.
2B. With short practice, this will become a rhythm ... place your cursor in the last name and double-click to highlight the word. If it's a compound last name, you'll have to highlight it all by hand. Use Cmd/Ctrl+X to cut the word(s) and put them in the clipboard. Then use the delete (Mac) or Backspace (Windows) key to remove the space between the given name and the surname you sent to the clipboard.
2C. Move your cursor to the start of the edit box and click to place the cursor before the first letter. Then press Cmd/Ctrl+V to paste the surname before the given one. Press the comma key, then the spacebar to separate the two names and you're done with level 2.
3. Click in the Level 1 edit box, and manually type in the award category (in this case, ART DIRECTION). Better to type in the award category than to risk transcription errors typing in names, and if there are any discrepancies you'll be able to fix those faster for the Level 1 entries. If this is the only index entry for Harry on the page, click the OK button to create a listing like the one below when you generate your index:
ART DIRECTION
Weber, Harry 12
Put the right index entry(ies) on the right page(s) and you won't have to worry about the wrong ones showing up. The entry drives what's assembled in the index text thread, so if you get that right, you've got it covered.
For multiple index entries – let's say that Harry scored the Grand Slam with all four categories for Best of Show on page 4 – the process is a little different:
4. After you fill in Harry's index entry for ART DIRECTION, click the Add button at the right of the dialog box. This makes the entry for that category/Level 1 index category. Then highlight and delete the Level 1 entry and replace it with CREATIVE DIRECTION. Hit the Add button to make the entry for that category. Lather, rinse and repeat for the TEXT category, then replace the TEXT entry in the Level 1 edit box with DESIGN and click the OK button.
This will create four separate index entries for Harry's Big Score on Page Four, one for each category he swept when he won Best of Show.
If you get the index entries right, the final index will reflect that. And after paying close attention for the first few entries you make, muscle memory will make this process second nature.
It will literally be a pain to do this 2000 times – take regular breaks, and expect that it'll take a few cycles to get back up to full speed after each break – but doing this manually will ensure you get the best, most consistent results. I keep a squeezable stress ball by my keyboard to resist cramping/carpal tunnel damage when I find myself forced to do these kind of duties. This will be a tedious, perhaps tortuous task. But not an insurmountable one.
I also bill through the nose for performing these services. If you're not able to do that because you've volunteered to do the award yearbook – just think of all the exposure you're going to get, they'll say – jack them up for other considerations to compensate you for the aggravation. They owe you one for this ...
Good luck,
Randy Hagan
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