I will pull lists from various sources myself, but from there I am looking to build a "system" of people and tools that automate the lead generation. 

There are plenty of free platforms out there that won't hurt your pocketbook but will automate a lot of the processes.

Look up the instrument and read it.

DST's are fee ridden instruments.  

Is there a way to pay him $270k "on paper" so he doesn't get hit with a long term capital gains tax at 15% and then pay him the remaining balance of $180k over time through a consulting agreement or other instrument where he would avoid the tax.

I just click a few times on my phone after I get an automated text message from Home away.

The others you throw away or work on them to conform to your business model.There are certain parts with technology that can be automated in the future but a majority want a human component with service.Maybe in 20 to 30 years those generations will want to do everything on their own.

Problem with Zillow is they have this annoying "1-click reply" where people can just click on your ad without reading it and you get an automated message "Joe is interested in your apartment at 123 Main St."

I've already set up automation systems for mining public records data and other lead sources.

The banks and funds will still bid - and they bid fairly low rates because even a 4% return is better than other very short-term instruments.