After all these responses my thought is to get the new style bracket and add an extra transom gudgeon strap above the bottom tiller strap.
Then I'd have three transom gudgeon straps for the bottom and one for the top. The top doesn't seem to need reinforcement from what I've seen. Bottom brackets are often an issue on any boat after all.
With this plan I'd only need to install one extra piece on the transom and so would have minimal room for error. I mean I'm handy but I don't want to get into more than I need to. I think I can get a SS pin from McMaster that is long enough for essentially 4 brackets.
I like gouvernails grocery bag approach to taking out slop, I used to use a plastic shim kit on my former boat and it was a pain to find the right shim. Fortunately for my situation, Wisconsin still uses plastic grocery bags, so they're easy to come by.