The landlord is required to repair EVERYTHING!

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.

Using these, you should be able to get most maintenance issues addressed in less than 90 days.One other thing, different tenants prioritize different repairs.

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

Find a renter, qualify them, move them in, collect rent, oversee repairs, re-sign leases, move them out, turn the unit, rinse and repeat.

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.

A seller could also refuse to pay any concessions for buyers closing costs, appraisal required repairs, etc. but it would be to their own detriment.

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

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!