It should buy time, and avoid legal fees being added to the balance as the foreclosure attorneys wont be involved for a while as they process you for different workouts.

How long it takes to be financially ready is different for everyone.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

I see it as no different from borrowing from a bank.

Because investing in NY real estate is a whole different game with taxes, regulations, and all that fun stuff.

If you have other money besides the 20K then this is a different story

Every job I see requires 3+ years of experience and knowledge of multiple different programs.

Still do your own math though....not that I wouldn't trust him, but every house and every neighborhood is completely different. 

Hey @Michelle Baldwin, yes this is a challenge but everyone said it best.Simply, you can just use a different browser to be logged into each VRBO account.I also think that @John Underwoods idea will work as well.

If someone came to me looking for money and was trying to invest across multiple asset classes as different as the ones you are interested in, that would leave me extremely weary.