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.

Question that the “believers” don’t ask is “how much could I earn on the extra money I’m spending to pay down the loan faster?  

If I was in your shoes I would find ways to streamline your day job so that you are not spending as much time in that role.

As a MF agent who spends a large amount of time calling apartment owners (or rather, numbers purporting to be apartment owners), please believe me that reaching out to random run down buildings owners is unlikely to get you any deals.

I took the next 5 months to tackle everything myself spending approximately 17k in supplies and tools + paying a plumber and roofer 4k total to fix those issues.

It's updated yearly and is the best $40 you'll spend as a Landlord. 

I would encourage you to learn the market you plan to invest in now and to continue to learn about the different methods of investing.

Where to spend the extra for durability and sometimes having to sacrifice aesthetics for durability, etc.

After spending 16,000 he's paying 2850.

There are a lot of options out there.Some of the most useful items BiggerPockets members have identified are features that save time so they can spend time working on their next property.