Has anyone entertained the idea of automating this process?

The issue is each month I am spending more time placing invoices, pictures, and other documents in folders, all which could and probably should be automated.

Not sure if it was a automated thing due to the date because house was dropping in price about every month month half and it was about that time.

Anything else though may not be worth your time or potential liability.True freedom is freedom of time, so if you can automate most parts of your business, then you're golden.

Then, is there an automated way that I can pay the LP their share based on the hurdles, catch-up needed to get to their IRR, etc? 

Free to use, easy to set up, and totally automated so once you set it up the first month you don't have to touch it again (it just automatically transfers the funds from the tenant's bank account to yours).

& as I am sure many of you know, the closing process after the PSA is signed is fast with a lot of folks and tasks.What is your favorite tech to use to assist with Investor/Fund raising reach-out workflow/process automation?

Between VRBO / Airbnb apps, automated templates, and your boots on the ground team it’s very easy and not very time consuming (once you get it going- initial setup on new properties can keep you a bit busy).The only requirement is having your phone on and with you 24/7 to quickly respond to inquiries & questions.

From 2002 to 2016 it is basically littered with the same thing foreclosures and collections including the state of Kansas.

My suggestion is, since you already chose your niche: buying residential  RE is to stick to this strategy until you have it automated.