I can have them just setup an ACH for the monthly payments, etc...but I feel like this would be easier with some automation, and there just must be something that's already setup for this.

Feel free to reach out to me if you have more questions. 

If you have any specific questions, feel free to ask—I’m happy to help! 

If arrears feel overwhelming, selling is the safer option to avoid foreclosure.

Another thing about most suburbs is that the property taxes can be brutal which needs to be factored in to your analysis.The biggest thing is where ever you buy, you need to feel comfortable living in AND upon move out, the property needs to cash flow. 

I have a feeling things will work out a lot better.

Meeting that 2 in 5 of the last requirement allows a single owner to shield $250k of appreciation and a married couple to shield $500k.Unless you predict a lot of income from the MTR or you feel that there is a lot of appreciation incoming over the next three years (minus time get the property sold), you may want to consider collecting your $100k (passing GO) and redeploying that money to whatever you feel is its best use. 

It feels like everyone and their grandma is on the Do Not Call list nowadays and my worry is the fines associated with accidently calling these individuals. 

I have a feeling the snowball of moment is increasing, and you will have that 4 plex in no time at all!

I feel you on this one.