I have found it very difficult to find an effective property manager to manage section 8 tenants.

What are effective ways to offer mentorship and coaching to new agents?

If you are looking at this decision through the investment lens, what would you net on the investment that you put this money in to, after transaction costs and taxes? 

If you were not, you’d save the same taxes as strategy 2  Or 2) You’re going to spend money (capex) that will be added to your cost basis giving you a higher yearly depreciation.

It's an effective temporary measure to buy a small amount of time to figure things out but its like poisoning the well, it will have long lasting effect on your personal credit and dismissing the BK won't change the credit impact.If you are doubting the validity of the lady's claim to the property, file a quiet title action and have her prove it belongs to her.

Financially speaking, I'm still saving, but the goal is 50k saved up (all costs: closing, fees, down payment, portion of rehabbing costs) by this summer with my fathers help on the cash all while I continuously save 50-80% of my work checks to fund for rehabbing this property and I work off my second job and "survive off of that."

Let's assume you don't take a loan.Purchase Price: $1,299,999Closing Costs: $25,000Renovate unit: $35,000Build 2 ADUs: $250,000TOTAL: $1,601,000The cashflow calculation looks like this:Gross existing rent: $5,600Gross rent from 4th unit: $2,500Gross rent from ADUs: $3,000TOTAL GROSS RENT: $11,10020% Expense Ratio: -$2,220Property tax: -$1,354TOTAL EXPENSES: -$3,574NET CASHFLOW: $7,526So, about 3/4 of your $2M budget gets you to about 3/4 of your $10,000/month goal.

Condition of a property and the cost to repair is just one of the risks in this business and you have to consider that in your buy price. 

Very little out of pocket cost. 

Food cost, Insurance cost, Drinking cost, eating out cost are all going up.