The calendars are synced, but that's the only thing we really have that is automated.

Avoid the large repositories offering just the automated data results.  

It is probable someone like a utility would not get noticed (sent a letter) in the bankruptcy, have an automated system for handling them and therefore their actions to collect would not violate the stay.  

I asked the potential tenants about the credit cards and he stated that he had a major medical issue 2 years ago and told the credit card issuer that he couldn't make payments, then he never heard anything else about it and didn't ever receive any more bills.To me this seems like some pretty significant red flags, yet the automated recommendation is suggesting that I should accept the tenant.  

Can someone recommend a couple of courses that focus on marketing prospects and processing leads that focuses on automation and scalability, that costs less than $1,000?

I know with a large number of rentals it has to be automated. 

. - when you do land those other units, it could be worth considering a shot at a software solution built for DIY landlords (1 - 15 units) to bring some automation to the rental management process, in turn, making things much much easier!

You can check around the forms, but there are many "smaller" PMS (like Hostfully or Ownerrez) that you can dip your toe into and set up a more automated, multi (listing) channel strategy.If I'm misunderstanding your situation, let me know, or send me a DM; I'd be happy to offer my advice on how you can stay hands-off.

Here are some ideas I didn't see you mention: Road Side Signs, Social Media Campaign, a Website (that can actually automate some of the stuff your Wife can't get to b/c of kids and life) and the last mention would be to form a Team.Real Estate Investing is not a 1 Man or 1 Family career, it's a Team Sport.

If you are looking to do massive amounts of mail pieces, you will definitely want to automate it with a mail house.