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

I probably will never be able to trust a large PM that automates away all the tenant/applicant contact. 

Automated billing with credit cards and what software is being used? 

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

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?

This is part of my business that I would like to automate but if you feel that timing is that much better with having checkbook control then maybe I will reassess my options.

I get automated listings from the MLS every day from my buyers agent.

@Larmon Cummings Jr  sending the same messages repeatedly is considered spam and triggers the automated filters. 

With Apartments.com I can automate rent payments, have the security deposit paid, and have tenants upload their proof of renter's insurance.Challenges of living with other roommates and renting by the roomWhen living with roommates there are always challenges.

As Greg stated above, Fannie Mae offers are submitted online via the HomeSearch portal, so it's a pretty faceless, automated process and you rarely get to talk to the man behind the curtain.