As you add more and bigger properties, you'll at some point likely transition to professional management, which will add more risk. 

Part of me thinks I may be better off passing this job off to a professional.

If you own a house near college you will feel stuck there or you will become a long distance landlord when you are a busy college student.Also once you finish college you may end up living in a completely different part of the country for graduate school, your first professional job, or some other adventure.

Especially on your first house.If you're buying commercial assets and/or seeking commercial financing (which is a higher risk, higher cost PITA), then do the LLC.Verify with legal/tax professionals of course @Kevin Dureiko

Contact lead and asbestos professionals in your area.

Private money lenders are usually not professional lenders and they don’t usually have their own lending documents.

Can anyone recommend a professional (I'm assuming a CPA vs attorney, but would like guidance) to help with this process?  

So the current stove has an electrical outlet behind, so does that mean he would need a professional to install a gas line by the stove?

Spread the word among professionals such as social workers, physical therapists, occupational therapists and speech therapists.Kudos for thinking about those who are presently under-served by the hospitality industry! 

However, looking for bargain-value requires a different skill set.