This is a commercial property so it doesn’t qualify as a Fannie Freddie non recourse deal...

I think the right answer is based on your personal preferences, goals, skills, abilities, and resources.

This property is owner-occupied which is how I qualified for the FHA loan. 

you will usually split a 50/50 equity deal for newbie investors but as you build your portfolio and experience you can start to weigh that more on your side. go to networking events and look for private money or if you qualify go with agency debt or some other loan product first

We got qualified stating it was based on renting our current place for at least $X per month with a minimum 1-year lease. 

BUT with him being new and potentially having the skill set to do other repairs in the future, I feel like this may be a good way to see his work ethic and talent to get jobs done in a professional manner, if that makes sense.

Remember that labor typically is the bulk of your cost especially when dealing with skilled trades.

I am having a hard time finding a property appraiser qualified to appraise property over 6 acres.Any recommendation?

You don't combine credit scores to qualify for a loan. 

I've enrolled myself in school to take a real estate course to get my license (cause I read somewhere, that that was necessary) and a business management course along with an accounting course to freshen up on my skills.