Would it be "Dangerous" to even pay out of my pocket on the first year to cover all expenses?

More cash flows from (it can, or it can't--it's risky) more run down areas (read that can be Dangerous areas) than the middle class areas, but they can cash flow too.Decide on if you are a Class B or C guy (Class D is usually not a good move for a beginner, due to the roughness and issues of the area).You will need a good accountant for taxes and bookkeeping, and an eviction attorney.You can self manage or hire a manager.Good Luck!

I also require 4x rent, since the over-the-top "tenant protection" laws in NYS took away many other mitigating factors for tenant screening (we cannot collect more then 1 month's deposit, cannot screen for eviction history, etc.).4x rent, and higher rent for those in dangerous territory.

This can be a dangerous “minefield” to travel through because it seems you want to help and fulfill the wishes of your father-in-law.

Flipping in a declining market as even an experienced investor is dangerous. this summer many new investors were taken advantage of by more experienced wholesalers and agents who were willing to unload deals and get paid.

This can be a dangerous “minefield” to travel through because it seems you want to help and fulfill the wishes of your father-in-law.

I know it is tempting to be the nice guy and approach them first, but you have a responsibility to yourself and your tenants to keep yourselves out of danger.

Your commission isn't paid until the deal closes, which means you're receiving $9,000 after you've already spent $9,000 on the deal.I think it's a dangerous precedent to spend money you haven't earned.

John, thanks for edifying me on the dangers of rentals that were converted which, I assume, is not of the same quality as a rental built for multifamily. 

@Steve Hyduchak  I'm a masters level social worker for my day job and serve on the board of the largest of the local substance abuse recovery non-profit.