I was one of the fortunate ones that was able to get out of the contract and after all expenses (forfeited deposit, legal fees, holding costs, etc) lost less than $20k.  

You can always consider doing a cost seg study on a property that you buy and that can also help with tax benefits if you cannot qualify for the real estate professional status.

Would you mind sharing the cost?

Nights, weekends, holidays, etc.To keep this on-topic, though...DO figure out what's healthy for you to manage but remember it's a process where every experience teaches you good and bad (and be patient with that process).DON'T sweat the small stuff (damage/costs under $50, undisclosed dogs, etc.) but DO find a way to learn, prevent, put in better practices to maintain your sanity. 

That's three months of mortgage and utilities, the cost of flooring, and the cost of painting.

Telling sellers everything wrong with their house and justifying your offer with repair costs doesn’t build trust—it kills it.

Can she pay you that same amount to cover some of the costs? 

That's why appraisers do the comparative approach and then secondarily the cost approach.So far, 100% of the time you don't get dollar for dollar back from what I've seen.

Do you feel like it has enhanced the productivity of your assistants to a magnitude that's worth the cost?

you may have to save up until you have enough money to do so - down payment, closing costs, reserves, etc.House Hacking: What Is It, How to Start, and Strategies for Successit's a more powerful way to get started.