I would like to somehow (hopefully), find a mentor to help guide me so I eventually partake in my first real estate investment whether it be wholesaling or owner-occupied property.

We are in 3 DOM market, These days even Owner / inexperienced buyers are super aggressive, I saw lot of broken homes are bought by owner occupant and not by flipper , if they don't care about all these mess/possibility to sue, then the job of buyer agent is simply a Docusign transaction exchanger.  

I'm personally not a big fan of arbitrage as it seems too many take advantage of the owner and don't create a win win. 

These folks had been through the wringer, mistreated and neglected by the previous owners.

She brought to my attention ongoing noise disturbances stemming from an improper flooring renovation conducted by the previous owner.

Angry tenants, neglected by the previous owner, greeted me.

Would they feel more of a pleasant experience while communicating with a business or the actually owners themselves?

HOA's take a substantial amount of control away from the owner and the monthly dues will always have a negative impact on your cash-flow.

The owner will want shorter term as possible due to his age. 

Have you considered renovating it to condo conversion and being the owner of both units, renting it, and then 1031 exchanging it into another asset?