I thought this calculator auto-calculated the monthly payment I see now that it didn't and I adjusted it to be around 3.7k and now it is making around $600 a month which seems more reasonable.

If you scale in the future, you can upgrade, but now you just need something that works and generates reports and takes auto payments.

It will cover whatever happens for your rental and your auto even your primary residence.

Auto or manual on /off?

I was thinking more auto shop, lawn care, electricians, etc.

I called my client rep, but got an auto-reply that she won't be back until 7+ days without leaving any contact.

There is rental software out there that can automate this for your, you can also set up auto emails to go out to your tenants.4.

ESS will auto send emails and text notifications to the tenants, which is a big time saver. 

I would use a software management software that people could pay online or setup auto pay.

I get their auto generated number and match up against the comps provided with the paid subscription.