More importantly why don’t you send money to TripAdvisor, Fairbnb, or booking.com?  

Now we know there are no free lunches, so it's important to understand the tradeoffs.

The most important thing is to start, so I wouldn't discourage you from buying.

This was important because I had a lender who would lend at 80%LTV. 

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.  

So far, I’ve worked on automating things like tracking expenses, sending out emails, and setting reminders for important deadlines.I’m wondering if anyone has any other suggestions for tasks I should look into automating to save time and streamline my workflow?

As a lender, it is my firm belief that honesty, transparency and service are the most important factors.

If not, I have included an article below that sheds light. 

What's important is to learn and move on.

That said, if you can afford it and have the reserves, and more importantly think you have a decent chance of increasing revenue with the vacant units then I'd probably go for it.