@Edward Toomey V It's unfortunate you had that experience with a software purposed for landlords; however, I'd hate for you to give up on software designed to work for landlords and ditch to QB.  

They have been the best investments I've ever made, but hoping to have greater cash flow influence with a daily business model.Is there demand for these types of rentals in the investment community?

It would be tricky to track billable hours accurately but I’m sure there is software to make it easier. 

I am sure there are more software that does the same thing and costs less.

What softwares are you using?

I'm tempted to do what many have said which is to just use a debit card, but I get 2% back on a CC, which is not insignificant when managing dozens of vendors, and I really hate to change a process that's working because the software I chose is lacking a basic feature.  

I'm a software engineer on a sabbatical trying to find my path out of the corporate world.Looking forward to connecting!

Also, since the books were several years old, I'm not sure if there is better software or apps like Zillow to use for managing a property.  

also look into AI powered softwares for narrowing down your search criteria. 

I've trained people at my jobs when I was a senior accountant to controller.I've used Yardi Enterprise (old desktop client software)Yardi Voyager 6s & 7sYardi Genesis2Reason why I say you won't be able to find a tutor is because no one is going to spend $15K a year to use as a training platform to mentor and tutor people.