Expanding from the bot from Hockey season Idea #2, once you have a functional analytic bot, why not make it enter a lot of fantasy drafts to train it.
To train the bot you could create your own pool and simulate against each other. Each one having a different approach and using a genetic algorithm to make it evolve each time.
Since the season takes a whole year, one way to make it work, is to train with the previous year and hide the training year from the training year.
Once they are trained that way, you can do multiple pools for the current year. Perhaps had an external choice in the mix. One of the teams could pick in the order of a listing from the news like hockey news or other NHL fantasy hockey predictions.
Adding human prediction to the mix
While using a listing from a web site or a draft kit is using human prediction they usually lack context of your hockey pool. To get the bot to train against real humans that make decisions in the context of the particular pool it needs to participate in the same draft we do.
The bot could participate in the multitude pool that are available online. If there is no limit on selection except for the cap, you could register a few bot as active players and make a bunch of others following the same format. (like TSN Pool etc) However, if it’s in a draft, a rotisserie or any kind of pool that a player can be only owned by one participant we need to be a bit more creative.
Beat the bot
Why not create an app or website where users can try to beat the bot. You can have a yearly draft where a limited number of people join to draft the whole league and there are 2-3 bots in the mix. It could be free and the site gives some kinds of prize if you finish first. It could also be paid and the money go toward the cash prize for those who beat the bot. Note that the second option could be considered gambling so I don’t know if it could work in all the states.
The second way to make it more dynamic is to have a weekly draft and include 2-3 bots in the mix, give a prize to the winner and if a bot wins you keep the prize.
How this can make money
A hockey pool is a great way to drive traffic to your site or app. Since they are games almost daily, users will log almost daily to check how their teams are doing. This is great for ads impression and you can offer a mailing list with the result and it should have a pretty high open rate. That money can go toward the giveaway and operating the site.
Giveaways could be done in partnership with other companies, brands, etc. This allows them to get new users to their list, follower count or whatever. You can get access to their user base and you might even not have to pay for the giveaway.