This came from my team and I negotiated the subto terms because she was motivated to sell, but had a mortgage higher than my cash price.

Good old fashioned calling someone up, sparking a conversation and finding out their motivation/pain points is definitely more effective than mailers.

Whenever reducing tax is your primary motivation, real estate is not for you.

Only the seller knows their true level of motivation to sell. 

But now, I believe I have the right amount of motivation to educate myself , start connecting with people, and learn from communities like this one. 

We contacted the tenant by email, by texting, and once talking telling that he has to leave at the end of the lease, but now the tenant does not want to communicate and does not pick up a phone.

And he is now avoiding all communications including phone, text, and email.

Fast forward...lessee texted me out of the blue asking me to call and told me about a pay raise that didn't happen and that he cannot afford the rent and wants out, asked for mercy and grace etc., and mentioned that I can keep the security deposit if I want. 

Anthony, Do not, I repeat do not take motivation from someone that tells you that you can't succeed in this business.

We were corresponding through text.