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

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've been working in software consulting services for over 15 years and it's kind of disheartening that I haven't been able to figure it out, but I've got other things to worry about (like how to get a few more properties so i don't have to worry about buggie tech crap anymore :) ).

Going forward it would be good to specify that your property management software is the only acceptable method of payment in your lease (if not done so already).It might also be a good idea to check the pre-existing lease to see if they have any clause like that (sounds like you already did that).

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.

Here are a few tools that I think might help you streamline your processes:I’d recommend checking out Bryt Software if you’re looking for something tailored to loan servicing.

Can anyone recommend software which would accept monthly payments (from me to seller) and create proper 1099 forms for tax purposes at year end? 

My first self-developed software gave me efficiency.  

I have totally given up on Quickbooks though it remains the best accounting software for the non CPA type 

But it would be nice to have access to the software and a place to basically wholesale the ones you don't want for yourself.