You’re talking about a 1099 contractor. You can think of them as a closer relationship than a handyman, but essentially you’re going to be on a dynamic, flexible system of give and take.
You’re also talking about potentially someone from the forums since they need to have one of your machines.
First, I would make sure you have a very clear statement of work. Things like: Proof reading the docs, making changes to the text and configuration in the docs, formatting the docs, creating and editing images for the docs, authoring new information into docs pages, pushing changes to github for review and publication. Authoring, editing, and publishing social media posts for V1E, etc.
You want to just say right away that cutting things out or maintaining their machine or hanging out on the forums is all encouraged, but explicitly not part of the paid job.
Then both sides have to trust each other a bit. Start with a discussion on the amount of time (and money) you’re willing to start with. It might be 20 hours over two weeks or 50 over a month or something. Design or planning meetings at the beginning of that time should be charged. A list of more specific tasks to work on should be agreed to and then the contractor would work towards them, while documenting their time. (As a former by the hour contractor, a digital timecard app in android/iphone is really helpful). If they get close to that allotted amount of time and they aren’t close to done, or they are close to done and need more tasks, then you meet again.
That way, neither of you should be surprised and the amount of work/money on the line is finite. The contractor would not want to jeopardize their future work by being dishonest and Ryan wouldn’t be writing a blank check.
There will be problems you should look out for. All the normal management stuff is going to be an issue. But specifically, Ryan is going to want to check in very often and he should avoid doing that. The contractor may have a question every couple of minutes that Ryan could easily answer. But they should try to solve it themselves first and collect a couple of questions at a time. The initial estimate for the amount of work will get done in a set amount of time will be wildly incorrect. So be prepared to be understanding on both sides. Some tasks may be explicitly time based. Like, “Spend 8 hours on the LR4 Jackpot instructions”. In those cases, you would want to see the actual pull requests that come out of it, and the contractor has to be responsible for staying on task over those 8 hours.
Eventually the relationship has to be cooperative or it won’t work. Both sides will have to trust each other. So there is a push to be explicit at the beginning (in the statement of work, to define the boundaries) and then based on cooperation and trust, with less specifics. It would waste a lot of good will and time to make the contractor document what they did every half hour, for example.
It really can work. There are definitely a lot of people that can’t do it with Ryan. Personalities are just like that. I’m assuming Ryan doesn’t have a lot of experience in management either, so he will have to grow too.