You can quickly see why looking at this graph - https://www.visualcapitalist.com/buying-vs-renting-house-in-...You can see how in 2015 the average mortgage was cheaper than the average rent, so it was easier to make the math work with light value add and just buying single family homes.

Are you not charging the guests a cleaning fee?

Selling vacant is easier, but if you can't/don't want to vacate the property investors will still look at tenant occupied homes 

Essentially I am looking for a clean way to organize everything as right now its very messy with how my current accountant is working things as he doesn't specialize in real estate.

But nowadays pvc or pex is an easier fix.

It is easier said than done. 

I've worked with several loan servicers, and no matter who you use, it's not fun setting it up, but I've had easier success communicating with OnePoint.They have a login portal to track payments etc, like you mentioned. 

They pay rent before the due date, clean the property after every client, and if something breaks they usually repair it before I'm aware because their clients will give them bad ratings.

The underwriting process is certainly more arduous than most acquisitions but through my personal experiences some of the lenders are far more knowledgeable about the requirements and make for a far easier process for both seller and buyer.

Easier to find two $1000 renter vs one $2000 renter.3.