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. 

That being said, thats the risk you run with every deal out there - that you might lose money and will need to eat the loss.I would definitely do it.  

At 95K cash I would want to see close to 25-30% return on my cash on a flip, because my time eats away at that return.

If you are using hard money, the holding costs during a crash can eat you alive. 3) Cash flow is almost always great and will save you during a crash.4) Having cash and getting good at raising money through rule 506 private placements or having access to self-directed IRA money will give you a huge advantage during a crash. 5) Underwriting hard money and selling the  notes on the mezzanine markets within 60 to 90 days  gets you high returns with old the risk of holding the paper.