Tenant/Buyer is required to put down nonrefundable option money.

If they are able to get it turned around and making money (cash flow positive), they then grab another one using a low-down payment loan.

I see a lot of unnecessary risk in investing in another country.If you still want to do it, I would start off with something on the lower end that is still nice to see how it goes for a couple of years before making a major investment out of country.I would thoroughly research all expenses such as taxes insurance, permits etc.

ALWAYS discuss w your tax advisor.  

Where can I go to borrow money to give the contractor in order to get the project started?

Make sure your accountant knows you lived in it for 2 years of the last 5 to avoid that cap gains tax.

Your cost of living sucks in NYC so that hurts as well.You say you want financial freedom, but what you really want is time freedom and the only way to get time freedom is through earning money to give you that.

what are you using the money for?

If you would have simply held on and collected rent for 72 months, you would have been up money...and that is buying at the peak right before the biggest real estate bubble in modern history.

I don't think it's worth paying for the repairs for a tax deduction, if the tenants want the AC they are welcome to pay for it themselves and they are.