I now realize how lucky I was to gain the vast exposure and experience I gained early in my career.

For me that number is $200,000.Liquidation Option: Sell all assets at a 50% loss, proceeds would only be sufficient to pay down a portion of the business debt, the rest would need to be covered with personal savings or income.

Outside of all the mistakes I made, which are clearly vast, what would one of you seasoned investors say I should do at this point?

The accidental genius was instituting sufficient controls to make sure his students are doing the work they're supposed to and not coasting their way to failure.If it gets you started and improves your life, it's a worthwhile investment, for you.

With decades of experience I can say the vast majority of "cash-cow" properties I, my clients, associates and friends have had started off with minimal to near 0 cash-flow.

For the vast majority of rental property investors who want a streamlined borrowing experience with a high degree of certainty that their loan will be funded on an accelerated timeline, DSCR loans are strongly preferred as long as property and borrower guidelines are met.

Therefore, even if I obtain a good value for the surface yield, it's possible that the Net Yield is unexpectedly low due to unexpected expenses.In Japan, the ideal yield varies depending on whether the property is new or used, the bank's interest rate at the time, and the real estate market conditions, but if the real yield on any property is 10% or more, the property is reasonably profitable and the cash flow is sufficient in many cases.

Finally, while on rare occasions real property does change hands a an extreme discount to market value, in the vast majority of the time a buyer, especially one without much experience thinks they’ve stump;ed across the “deal of the century”, they’ve mispriced the actual value because of something not readily apparent hasn’t been considered.  

If I start running it as STR starting in June of this year, do I have sufficient time to meet material participation?

Mold requires water and a food source (dust is sufficient), so it's important to find the source of water and stop it.