Your comment history shows you are not one of those. I think if you had written ".... wrestling website I run." you would improve the chance of getting some feedback from other HNers, because it's a more personal connection.
My market is completely different from yours. All I can offer is encouragement in your effort.
As someone with no interest wrestling, I browsed around a bit out of curiosity. Would it be reasonable to add more links? You have the Twitter handles, but I have to copy/paste to get there, and there is no home page. These could be linked, by icon, inside the the ws-header for the school page.
Will there be (possibly user-submitted) links to photos from recent meets? What about links from the upcoming tournaments to the web site for the tournament?
I don't think it's that important for most people to see "This is a cached page, it was last updated: 9/16/2016 10:43:18 PM" / "View version: Click here for live version | Cached version" right at the top of the content. Even if they cared about cache status, I think "Last updated 5 seconds ago" would be easier to interpret. Especially as it isn't 10:43:18 PM in this time zone.
I realize this is all extra work, and you are self-funded. Feel free to ignore me!
Again, best of hopes that it goes well, and that you figure out a good funding model.
Regarding your feedback, THANK YOU! I like getting feedback from more technical people.
Yeah, that date (format) is really annoying to look at now that you bring it up. Makes much more sense to have it like you state (5 minutes ago...).
More links - I thought I had WAY too many links (been trying to figure out the SEO stuff also). Just about anywhere in the site where you see either a wrestlers name, or a school name, they are always links (except when they are in headers). I can definitely add the links in the headers, the side-effect to that is then they'll be underlined.
Cool idea on the photos and links to registration sites. Be fun way to interact with each of the "events" and feel more like you were there.
Thanks again for the feedback, I'll definitely work on most/all of those!