Those other probs have now gone away plus I'm making a lot more dough from my regular work/day job these days.

For most loans especially for first time homebuyers, your lender wants to see a 2 year work history of the same job that you are or will be working (same thing if you are self-employed).

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.

Keep your job as long as you can.