I cook meals at home, and we eat leftovers for lunch.

We where spending thousands a month eating at Landry's restaurant I guess. 

Talk about having your cake AND eating it too!

I've tried zillow and loop eat but it's difficult to narrow down the results.

I've been basically eating, sleeping and breathing REI learning and connecting with others before even considering taking on my first deal, the reason isn't out of fear well okay maybe it is a little bit but mistakes in this business can cost you big.

., he will have to feed this property every month or it will eat him alive.

However, since you'll be renting the places out, do you want to eat the repairs later or replacement now?

The property taxes are eating up most of the rent every month. ( $1700 / m ). 

If you can get in on the low cycle and sell on the high you could make some money but you'll work for it by renting in between and holding costs will eat your profit. 

The owner is a really old lady that has just been eating property taxes and insurance for an insane amount of time but is clearly not super motivated to sell it for some unknown reason.