Because your counterparty is going to be Joe Schmo rather than a professional institution which will likely add some challenges that you're not used to. 

If you want to use a professional to buy or sell, you are responsible to pay a professional's fee.

Else the tendency to not care and not treat the arrangement with respect, may arise.  

I would do this carefully through a trusted mortgage broker. - You could also house hack again

There will be people who say to be weary of it because of turnover or the threat of damage and ruining aspects of the property but if you can tolerate it or find tenants you feel will take care of it well, it could be a good route to go on.

I'm a golf professional working near San Jose, CA.

Are there people that you can send to the auction like a professional bidder?

As in my case, working as a full service Property Manager, I'd imagine that would instill more confidence that a building will be taken care of, units will be leased, preventative maintenance will be done, etc.

Long term, buyers still want and need professional representation (in most cases) particularly for more complex transactions, investors from out of the area, or relocation buyers. 

Since I want more hands off approach these are appealing but I want to be careful.