If you are setting aside funds for capex, taxes, insurance, or other expenses that don't occur monthly, transfer those funds to Savings each month and hold them there until it's time to spend them.

Don't spend time looking for something that doesn't exist.

Insurance doesn't cover anything anymore and we can almost just pay for all damages with the money we spend on it! 

A lot of people spend their time doing this, but it's not a good use of time because it can not teach you anything relevant without seeing each one in person.

We plan to spend the next 6-12 months continuing to earn and save, as well as nail down a final market we want to househack in.

Spending on expensive upgrades is not the answer to improve your tenant base in this type of area.Keep the homes habitable, clean, and safe. 

You definitely wont get an app like that for free, so how much would you be willing to pay to a company to submit it for you, vs spending 10 minutes once a month to submit taxes? 

Like @Jesse Rivera mentioned above, I also go to a few sessions but spend most of my time in the lobby or at the bar making connections."

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.

You spend a giant pile of money before you make a dime of revenue.