HML costs a lot of money and can be a pain to deal with sometimes.

Do the brokerages offer health insurance for full time and part time agents?

It's not especially clear to me from your post whether this is an existing facility or a ground-up development since you said, "it's a very nice, higher end facility" and earlier had referenced "a self storage development site" so if you are looking at an existing facility, by all means, get painfully clear in the due diligence phase. 

It is probably better to invest in a BRRRR if it is an add-value product.The more units at each address is usually better and it is less painful with a vacancy. 

I have a mixed use property under contract that was a pain to get financing for because the residential lenders didn't want to touch it due to the commercial building.  

@Ryan Hanrahan when I was talking to a seller about potentially buying his property I built rapport with him and found out all his pain points.

Thoughts on getting a part time job for health insurance?

Individual loans under a single LLC or corporation would a bit of a pain (6 appraisals, 6 closings, etc) but easier to do from an underwriting standpoint. 

However, new laws mandate safety, health requirements are to be disclosed, changed especially dealing with non conventional loans.

Also, I would be careful not to discriminate against him for any mental health disabilities he might have, since your actual concerns are the threats to other tenants.