It sounds like you got caught up in a automated process that is not personalized and still a rough.

We have automated filters which catch a lot of stuff.

That way, you can also automate reminder emails and late fees.

First things first, I don't have any experience in this field yet, so I'm wondering if this is too big of a feat to take on for my first attempt, or would using software to automate things make it possible to manage this many units?

Mainly, the systems implemented are fascinating (VA, automated offers, etc.)

Automation can sometimes lead to the data being jumbled.Consider Premium Listings:When you do a property search on any major website, you will likely see certain properties at the top time and time again.

I find cash buyers and the new List Automator works well for me. 

No seasoning.Key Bank, flexible lender, HELOCs on second homes and rental properties.PenFed - max 3 other propertiesLendingTree is a broker, connects you with multiple loan providers, some sub prime.TD BankTower FCU, all states except TX, Automated appraisal.TrustcoUnion BankUS BankFigureGood luck

After that get automated with your reminders.

As far as automation goes, there will always be more technological advances that make agents work harder, but even Mcdonalds that is going extremely automated still needs humans to run the business.