It auctioned off to some online bidder for 30k! 

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

I am curious if other investors create a business plan or provide other documentation to loan officers?

I've noticed the forums provide a wealth of knowledge from individuals investing in a wide variety of strategies and feel this is the best place to start.

There’s lots of property managers and service providers that come.

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

I see these four rentals providing us a regular stream of income during retirement. 

@Phillip Rosin - Based on the info you provided, I recommend that you start with a Fix to Rent short term loan to purchase the property and rehab it, followed by a cash out refinance into our DSCR loan.

Jeff, I know it's been awhile since we've chatted and I've massively improved my online resources for everything you listed here... neighborhoods, PM's, accurately running numbers, etc.Happy to email that stuff over if you want.

If you want to remote investment and / or turnkey, be sure you vet your providers and management companies thoroughly.