City employees generally get the job done in one week, third parties can take two weeks to get this done.

For liability I'm thinking if someone gets hurt on the job site, we find out the home building materials were toxic, something along those lines. 

Your realtor will do a lot of the acquisition hand holding you're looking for and BP and your local network can help with any concerns you have getting folks into the property and managing it, or you can hire a property manager to do it, albeit at 10-15% of gross and they won't do as good a job as you will.

Good job saving yourself hundreds with a single phone call!

I am kind of stuck on where I should lead him next, since he's busy with school and sports he doesn't have time for a job.

It’s easy to find tenants, population/jobs are increasing, and property taxes/insurance aren’t skyrocketing. 

With my interest in learning more I have researched or looked for jobs nearby but I have noticed that the design community in Eugene is fairly small and most seem to only be a one person job.

Also the tenants job turnover seems to be much higher. 

Mark zuckerberg, bill gates and steve jobs also dropped out of college.

Keep your job as long as you can.