[Arrath]

>I'm doing a bad job of formulating tasks, and that this is a skill I need to get better at, but has anyone found success with hiring an assistant?

I would start with this point. Take some time, be it weeks or a month, and every time you come across one of your one-off tasks that you would love to delegate out, note it down.

Later on, try to document or at least bullet point those tasks into something more well described, workflow, deliverables, average time to complete, etc.

Once you have a stable of such tasks you can then condense them back down to a job description that will help your search a lot. I did this prior to hiring an assistant and it worked great. I had a list of tasks to post, and to discuss through the interview. I knew which programs I would be asking the interviewee to have experience in, and I had an idea for further tasks to be added to the workload if things worked out, which they did!