Ask how many units they manage and how much experience they have.

My experience was mostly doing SFH/Duplex/Triplex etc. and had experience in larger multifam. 

I think a great strategy would be to find someone who would like to house hack with you, and maybe even someone with a bit of experience local to the area that you trust and know very well to go in on the deal with you.  

Does anyone have experience doing this?  

We were wondering if it would be best for him to get the degree or to drop out and focus on making money and getting experience in real estate instead (or try and do both)? 

Partnering: If you're initially short on funds or experience, consider partnering with someone who has more experience or capital.

Any advice on this and experience/tips from others having gone through similar deals would be greatly appreciated!

Keep in mind, such an appraisal may not be able to be used by your lender, but perhaps you can request an appraiser with investment property experience (wherever they may be). 

Ask how many units they manage and how much experience they have.

At this time the primary goal is passive income and then scale within 5 years as I gain more experience and network.