It sounds like your assets will exceed the exempt assets allowable in New York for a Chapter 7 case amongst other apparent issues. Since the devil is in the details, you need to identify each house by fair market value and the outstanding mortgage balance to determine what your actual equity is. In addition, the Courts are not keen on keeping more real estate than your actual residence and not paying your debts.
The "you" in your question "can" file for personal bankruptcy. The question "you" should be asking instead is what the likely result would be. "You" may have primarily non-consumer debts, which eliminates the means test and any motion to dismiss for abuse from the picture. "You" probably has too much debt for a Chapter 13, however, so Chapters 7 and 11 would be the available choices. Chapter 11 is very expensive, and something call the "absolute priority rule" may prevent "you" from keeping any assets, depending on how the judge intereprets that rule in light of the 2005 BAPCPA amendments. In Chapter 7, all non-exempt property would go to the case trustee for liquidation. Living in the house that has the most equity might allow a homestead exemption for that property.
"You" would be foolish to proceed without the advice of a NY bankruptcy attorney. Tell him (in the shaving mirror, if necessary) to hire one instead of relying on free online advice.
Too many details to know if you can file bankruptcy. Put a list of your assets and debts together and meet with an attorney. Include among your debts all business contracts that you have guaranteed.
Business bankruptcy Chapter 7 bankruptcy for businesses Chapter 13 bankruptcy for businesses Liquidating business assets Business real estate Bankruptcy Chapter 7 bankruptcy Chapter 7 bankruptcy means test Bankruptcy petition Bankruptcy court Bankruptcy documents Bankruptcy exemptions Bankruptcy homestead exemption Chapter 13 bankruptcy Debt Bankruptcy liquidation Bankruptcy and debt Chapter 13 bankruptcy reorganization plan Real estate and bankruptcy Real estate Business Motion to dismiss