Renovations and Repairs- The property is  a ~100yr old brick  building and will require some work before its rent ready. 

That HE loan would make you cash flow negative on the first property, especially considering you are not even factoring in any repairs, maintenance, vacancy or management.

Other than that, the city is largely residential with many jobs focused around providing for those residential needs such as the service industry sector, home repair, construction, etc.

There's not many tools in the box to repair many years of poor policy i.e.

The plumber will likely have to cut open the ceiling to confirm and make repairs, so you can save a little money by learning how to do that yourself, confirm the problem, and then call the plumber for repair, then patch the ceiling yourself.As Jonathan is trying to point out, it's important to expect these things and have funds on hand to deal with them.

If the water would have came back bad we were prepared to replace the pipe but was told this repair would be around $8K. 

(I would not specify how much.)If the property needs a ton of repairs, then even buying it subject to the existing mortgage may not be enough to make this a viable deal.You need more info, and fast!

But what you will find is that most repairs are pretty easy - and if we don't want to mess with it we will call someone ourselves... but someone we know is going to shoot us a fair deal.

Hoa said that we need to change/repair driveway otherwise we will be fined. 

And yes, I know people will say "get her in contract if she wants the house and perform repairs" that would be the best scenario except At that point I was completely out of money.