cause the house is so small and the land so expensive in Westchester county.So does it make sense to just rent it out every year having someone else "pay" for the house?

Form an addendum that Jack and Jill sign where Jill acknowledges she will be taking over for full rental payments, damages to the property, and security deposit (would not recommend giving half back to Jack you could argue this would cover him getting of his lease agreement early).  

One thing I did was get my own insurance policy and glad I did because I incurred 12K worth of water damage about a few months later after the transaction.

It's not as much the hurricanes (the roof on a block house is still wood frame) it's the termite damage.

You will either spend a lot of time or some money to be a successful wholesaler, however if you can get roofing repairs done at a significant discount you may want to try and target homes with roof damage that an owner may not be able to afford.

The warranty company denied our claim because they said corrosion in the coil caused leakage which isn’t covered.

There is a clause that basically says " any delays that are caused by the customer or any other contractor on the job resulting in loss of time or delays or damage will be billed as an additional cost to the customer at XXXX  $ per man hour plus materials .  

I have picked up $1600 refrigerators for $500 and all the damage is to the back side that was not even seen.

We couldn't get access to see the downstairs space so we couldn't even see the damage or estimate repairs.

Hello,Long story short:  Tenants didn't pay last month's rent and damaged carpeting with smoking (prohibited in lease) and other stains, left significant junk to be cleaned out and some other damages.