You need to make sure you include Property Management (20%), cable, electricity, gas, sewer, home automation devices, pool maintenance, rental permits, etc. 

I see some places have automated the system but curious if it’s worth the money. 

The only systems that I have built so far are automation of rent payments and mobile inspections.

No, all of my tenants pay thru ACH (automated clearing house).  

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.