You may want to consider a similar approach.While having an experienced PM and knowledge is beneficial for you, it means very little to a broker or seller. 

The only instance where it might be more beneficial to do it this way vs. getting financing right off the bat is if you need to be SUPER competitive with your offers in your market.

Or, would it be beneficial to hire an employee to handle day to day tasks?

So, factor that into your thinking about whether its the right choice for you. 4.

I would thank him for his feedback and share that you made a business decision that is mutually beneficial (https://www.avail.co/education/articles/should-you-collect-r...scroll down towards the bottom of the page to see the comparison) which includes providing the tenant with a receipt and rent reminders.  

He had no choice but to begin selling off the portfolio.

Like mentioned it's also beneficial to keep up to date with what's happening in the area your STR is located, and make sure the decision makers are aware of hosts and what they bring to the community.

I’ve never actually been legally owed money before so I was green on how to handle things while trying to be understanding and respecting other lifestyles and career choices.

They made it sound like it was something easy to comply with, but if anyone who is a beneficial owner has their ID expire or they move, you have 30 days to re-submit the paperwork.  

Facebook groups can be quite beneficial as well.