My thought is to put together a very detailed set of instructions including a screencast. Then contact one of the many companies that offers virtual personal assistants. Tell them you need someone for a couple hours a week with whatever level of technical knowledge they'd need to be able to follow your instructions.
Then start using them right away (before being interred) so that you can see if you've gotten a person who understands the task and can do it well, or if you need to have them find someone else to do it.
It should be cheap and easy.
Alternately, you could just sell the business and start a new one when you get out. I'm sure there are many folks here, myself included who would be willing to consider buying a self-sufficient SaaS business.
Then start using them right away (before being interred) so that you can see if you've gotten a person who understands the task and can do it well, or if you need to have them find someone else to do it.
It should be cheap and easy.
Alternately, you could just sell the business and start a new one when you get out. I'm sure there are many folks here, myself included who would be willing to consider buying a self-sufficient SaaS business.